BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose...

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BIOCHEMISTRY Carbohydrates BIOB111 CHEMISTRY & BIOCHEMISTRY Session 11

Transcript of BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose...

Page 1: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

BIOCHEMISTRY

Carbohydrates

BIOB111

CHEMISTRY & BIOCHEMISTRY

Session 11

Page 2: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Key concepts: session 11From this session you are expected to develop an understanding of the following concepts:

Concept 1: Classes of carbohydrates: monosaccharides, disaccharides and polysaccharides

Concept 2: Interpreting the names of simple carbohydrates

Concept 3: Location of the functional groups in an aldoses and ketoses

Concept 4: Cyclic and acyclic sugar structures

Concept 5: Glycosidic bonds

Concept 6: Breaking down multi-subunit sugars

Concept 7: Cellulose in the diet

Concept 8: Digestion of polysaccharides vs disaccharides/monosaccharides

Concept 9: Glycogen

These concepts are covered in the Conceptual multiple choice questions of tutorial 11

Page 3: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Session OverviewPart 1: Monosaccharides

• Classes of carbohydrates

• Straight-chain monosaccharides

• Monosaccharide: glucose

• Monosaccharide: galactose

• Monosaccharide: fructose

• Monosaccharides in DNA and RNA

• Cyclic monosaccharides

Part 2: Disaccharides

• Glycosidic bond

• Digestion of dietary carbohydrates

• Disaccharide: Maltose

• Disaccharide: Lactose

• Disaccharide: Sucrose

Part 3: Polysaccharides

• Digestible vs non-digestible polysaccharides

• Polysaccharide: glycogen

Page 4: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Part 1: Monosaccharides

• Classes of carbohydrates

• Straight-chain monosaccharides

• Monosaccharide: glucose

• Monosaccharide: galactose

• Monosaccharide: fructose

• Monosaccharides in DNA and RNA

• Cyclic monosaccharides

Page 5: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Functional groups in carbohydrates

Page 6: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Classes of carbohydrates

• Plants produce carbohydrates via photosynthesis

https://www.freeimages.com/photo/a-leaf-1488203

• Plants utilise carbohydrates for:

– Structural support (e.g. cellulose)

– Energy (e.g. glucose and starch)

Page 7: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Classes of carbohydrates

Functions of Carbohydrates:

• Can be metabolised to generate energy for plants and animals

• Form supportive structures in plants (cellulose),

insects and crustaceans (chitin)

• Provide short-term energy storage in plants (starch) and humans (glycogen)

• Carbohydrates are:– Important components of DNA and RNA molecules

– Structural components of cell membranes (glycolipids)

– Involved in cell–cell and cell–molecule recognition processes (glycoproteins)

Page 8: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Classes of carbohydrates

Glucose

Single sugar unit

Glucose Glucose

Two sugar unit compound

Many, many sugar unit compound

Monosaccharide:

A single unit sugar is a monosaccharide

Disaccharide: A compound made up

of two sugar units is a disaccharide

Polysaccharide: A compound consisting of Between 100 and 1 million sugar units is a polysaccharide

Page 9: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Classes of carbohydrates

Monosaccharide: A single unit sugar is a monosaccharide– Examples:

– Functions:• Monosaccharides connect together via glyosidic bonds to create multi-unit sugars

(disaccharides and polysaccharides)

• Monosaccharides can be metabolised by humans to generate ATP (cellular energy)

Glucose

Single sugar unit

Glucose Fructose Galactose

Page 10: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Classes of carbohydrates Glucose

Disaccharide: A compound made up of two sugar units is a disaccharide– Examples:

Glucose

Two sugar unit compound

Glucose Glucose Glucose GlucoseGalactose Fructose

Maltose Lactose Sucrose

– Functions:• In a disaccharide, the two sugar units are connect via a glyosidic bond

• Disaccharides can be broken down into two individual monosaccharides– The monosaccharides can be metabolised to generate ATP (cellular energy)

Page 11: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Classes of carbohydrates

Polysaccharide: A compound consisting of between

100 and 1 million sugar units

Examples:

Many, many sugar unit compound

https://www.freeimages.com/photo/baked-potatoes-1532388

https://www.freeimages.com/photo/a-leaf-1488203

https://www.freeimages.com/photo/the-bug-1180812

Starch Cellulose Chitin GlycogenGlycogen is an energy storage compound that is found in the liver and muscle

Glycogen is broken down into glucose units at the beginning of a run to provide quick energy generation

Cellulose provides structural support to plants

Chitin is found in the exoskeletons of insects

Potatoes are a starch rich food

Starch is made up of many glucose units which are slowly released into the blood as digestion occurs

Page 12: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Straight-chain monosaccharides

• Straight-chain monosaccharides contain many alcohol groups

– The straight-chain monosaccharides contain either a single ketone or aldehyde group

– Monosaccarides that contain the aldehyde functional group are called Aldoses

– Example: Aldohexose is a 6 carbon monosaccharide with an aldehyde functional group

– Monosaccarides that contain the ketone functional group are called ketoses

– Example: Ketopentose is a 5 carbon monosaccharide with a ketone functional group

Page 13: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Straight-chain monosaccharides

• Where is the non-alcohol functional group located in the compound?

At the top of the compound

• What is the non-alcohol functional group present in the compound?

The aldehyde functional group

• Is the carbohydrate an aldose or a ketose?

The monosaccharide is an aldose (contains the aldehyde functional group)– The compound contains 6 carbons

– The compound is glucose

Page 14: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Straight-chain monosaccharides

• Where is the non-alcohol functional group located in the compound?

Near the top compound between two carbon atoms

• What is the non-alcohol functional group present in the compound?

The ketone functional group

• What class of carbohydrates does the compound belong to?

The monosaccharide is a ketose (contains the ketonefunctional group)– The compound contains 6 carbons

– The compound is fructose

Page 15: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Straight-chain monosaccharides

• Some compounds including glucose can exist either in

a right-handed (D) or left-handed (L) isomer

– Both the L and D isomers are called stereoisomers

– Stereoisomers are the mirror image of each other at a specific position within the compound

The right handed isomer

is called the D isomer

– Dextrorotatory compound:

A chiral compound that

rotates the plane of

polarized light clockwise

(to the right)

The left handed isomer is called the L isomer

– Levorotatory compound: A chiral compound that rotates the plane of polarized light counterclockwise (to the left)

Right-hand sideLeft-hand side

D-Glucose L-Glucose

Note: L-glucose is not found in nature but can be created in

the laboratory

Page 16: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Attempt Socrative questions: 1 to 4

Google Socrative and go to the student login

Room name:

City name followed by 1 or 2 (e.g. PERTH1)

1 for 1st session of the week and 2 for 2nd session of the week

Page 17: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Monosaccharide: glucose• Straight chain D-glucose is an aldohexose

– Contains an aldehyde functional group and six carbon atoms

– D-glucose is the most abundant monosaccharide in nature

D-Glucose

• The body relies on glucose to perform many metabolic reactions including glycolysis– Metabolic reactions are required to generate cellular

energy (ATP)

– Carbohydrate containing foods are the body’s main source of glucose

• The body can make glucose from pyruvate and oxaloacetate using gluconeogenesis

Glucose

Page 18: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Monosaccharide: glucose

• The level of glucose in the blood (blood glucose)

must be maintained within a fine range:

3.5 – 5.5 mmol/L of blood

– The blood glucose level is maintained by the hormone

pair insulin and glucagon

D-Glucose

• Glucose is delivered to the organs and tissues via

the blood to allow the cells to generate energy

– The brain is very dependent on glucose as it cannot

create energy from lipid (fats and oils)

Glucose

Page 19: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Monosaccharide: glucose

• Insulin

– Insulin functions to bring glucose into the cell from the blood

• Insulin assists in lowering the blood glucose level when the blood glucose level is high

– Insulin promotes metabolic reactions that use glucose

• Glucagon

– Glucagon functions to

move glucose out of the

cells into the blood

• Glucagon assists in

increasing the blood

glucose level when the

blood glucose level is

low

– Glucagon promotes

metabolic reactions that

make glucose

Cell

Blood

G

Insulin

G

Glucagon

G = Glucose

G

G

Page 20: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Monosaccharide: galactoseGalactose

D-Galactose D-Glucose

• Straight chain D-galactose is an aldohexose just like glucose

– Contains an aldehyde functional group and six carbon atoms

– Only difference between galactose and glucose is the position of one alcohol group

Page 21: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Monosaccharide: galactoseGalactose

• D-Galactose is a component of the

glycoprotein responsible for the ABO

blood groups

– The glycoprotein is present on the outside

of the red blood cells (RBCs)

– If an individual who has type A blood was

given type B blood, the individuals immune

system would attack the new RBCs

• The B antigens on the RBCs are recognised

by the immune system as non-self

Page 22: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Monosaccharide: fructose

• Straight-chain D-Fructose is a

Ketohexose

– Contains a ketone functional group

and six carbon atoms

D-Fructose

Fructose

Page 23: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Monosaccharide: fructose

• D-Fructose is the sweetest tasting sugar

– Found in fruit and honey within the disaccharide sucrose

• Sucrose contains one fructose and one glucose

• D-Fructose cannot be stored by the body

– Fructose is metabolised by the liver

– Excess fructose can cause the accumulation of fat (triacylglycerol in the liver)

• Occurs via the lipogenesis pathway

Fructose

Glucose Fructose

Sucrose

Page 24: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Monosaccharides in DNA and RNA

• Both DNA and RNA contains sugar units

(monosaccharides)

– A single unit of DNA and RNA is called a nucleotide

• A nucleotide contains:

– One sugar (ribose or deoxyribose)

– A nitrogen containing base

– A phosphate (polyatomic ion)

Page 25: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Monosaccharides in DNA and RNA

Sugar present in DNADeoxyribose

Sugar present in RNARibose

Contains one less oxygen atom than the ribose sugar

Page 26: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Cyclic monosaccharides

• Monosaccharides with 5 or more carbon atoms

can exist in either a:

– Straight-chain structure

– Cyclic structure

Straight-chain D-Glucose

Cyclic D-Glucose

Page 27: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Cyclic monosaccharides

Straight-chain D-Fructose

Straight-chain D-Glucose

Cyclic D-Glucose

Cyclic D-Fructose

KetoneEther

Ether

Aldehyde

• Straight-chain sugars lose their aldehyde and ketone functional groups when they become cyclical sugars

– Cyclical sugars contain the ether functional group

Page 28: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Part 1: Monosaccharides

• Classes of carbohydrates

– Single sugar units are called monosaccharides

– Disaccharides contain two sugar units connected together

– Polysaccharides contain between 100 and 1 million connected sugar units

• Straight-chain monosaccharides

– Aldoses contain the aldehyde functional group

– Ketoses contain the ketone functional group

– Straight-chain monosaccharides can exist as either an L or D-isomer, with the L-isomer being

the left-handed version and the D-isomer the right-handed version

• Monosaccharide: glucose

– Straight-chain glucose is a six carbon containing aldose sugar

– The body relies on glucose to generate cellular energy via metabolic pathways

– The hormones insulin and glucagon maintain the level of glucose in the blood within a

specific range

– Insulin lowers the blood glucose level by moving glucose out of the blood into the cells

– Glucagon increases the blood glucose level by moving glucose out of the cells into the blood

Page 29: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Part 1: Monosaccharides

• Monosaccharide: galactose– Straight-chain galactose is a six carbon containing aldose sugar which

has a very similar structure to glucose

– Galactose is present within the antigens on our red blood cells

responsible for the ABO blood group system

• Monosaccharide: fructose– Straight-chain fructose is a six carbon containing ketose sugar

– Fructose is the sweetest sugar

Page 30: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Part 1: Monosaccharides

• Monosaccharides in DNA and RNA– Each individual unit of DNA and RNA is called a nucleotide

– Each nucleotide contains either a ribose or deoxyribose sugar

– The only difference between ribose and deoxyribose is that

deoxyribose contains one less oxygen atom

• Cyclic monosaccharides– Monosaccharides with 5 or more carbons can exist as either a cyclic

or straight-chain structure

– Cyclic sugars contain the ether functional group instead of an

aldehyde or ketone functional group (present in straight-chain sugars)

Page 31: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Part 2: Disaccharides

• Glycosidic bond

• Digestion of dietary carbohydrates

• Disaccharide: Maltose

• Disaccharide: Lactose

• Disaccharide: Sucrose

Page 32: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Glycosidic bond

• Glyosidic bond formation– Two cyclic monosaccharide sugar units connect together in a chemical reaction,

where an alcohol group from one unit reacts with an alcohol group from the other unit:

• Alcohol + alcohol → ether

– The ether functional group connects the two monosaccharides together to form a disaccharide

+O

OHOH

HO

OH

CH2OH

O

OHOH

HO

OH

CH2OH

O

OHOH

HO

OH

CH2OH

OO

OH

OH

CH2OH

+O

HH

Glucose Glucose Maltose H2O

Glycosidic bond

Page 33: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Glycosidic bond

+O

O

OHHO

OH

CH2OH

O

OHOH

OH

CH2OH

Glucose Glucose

O

HH

H OH

Glycosidic bond connecting the two

glucose units together

Maltose disaccharide

Animation of glycosidic bond formation

Ether

Page 34: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Digestion of dietary carbohydratesDietary carbohydrates

STARCHSUCROSELACTOSEMALTOSE

ONLY MONOSACCHARIDES ARE ABSORBED INTO THE BLOOD VIA

THE SMALL INTESTINE

TRAFFICKED TO THE LIVER CELLS TO BE

METABOLISED INTO CELLULAR ENERGY (ATP)

MONOSACCHARIDES: GLUCOSE, FRUCTOSE

AND GALACTOSE

Common dietary carbs

Digestive enzymes facilitate the breakdown of the dietary carbs into monosaccharides by breaking the glycosidic bonds which connect

their sugar units

Glucose, galactose and

fructose TRAFFICKED TO OTHER CELL TYPES INCLUDING

THE BRAIN AND MUSCLE TO BE

METABOLISED INTO CELLULAR ENERGY (ATP)

Glucose

Page 35: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Disaccharide: MaltoseD-maltose = D-glucose + D-glucose

• Two glucose units connected via a glycosidic bond forms maltose

• Maltose is produced during the breakdown of starch

in the digestive system

Glucose Glucose

Maltose

Page 36: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Disaccharide: MaltoseD-maltose = D-glucose + D-glucose

• Maltose is broken down into two glucose units in a chemical reaction facilitated by the maltase enzyme

– The maltase enzyme is present in the small intestine

• Once maltose has been broken down into two glucose units in the small intestine:

– The glucose is absorbed into the blood and trafficked to cells for metabolism

O

OHOH

HO

OH

CH2OH

OO

OH

OH

CH2OH

+O

HH

Maltose H2O

+O

OHOH

HO

OH

CH2OH

O

OHOH

HO

OH

CH2OH

Glucose Glucose

Maltase

Page 37: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Disaccharide: Maltose

OO

OHHO

OH

CH2OH

O

OHOH

OH

CH2OH

Glucose Glucose

O

HH

HO

H

Maltose disaccharide

Animation of the breakdown of maltose

One alcohol functional group created on each glucose unit

Page 38: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Disaccharide: Lactose

D-Lactose = D-Galactose + D-Glucose

• The galactose and glucose units within lactose

are connected via a glycosidic bond

• Lactose is commonly found in milk

Glucose Galactose

Lactose

https://www.freeimages.com/photo/milk-and-cookies-1545267

Page 39: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Disaccharide: Lactose

D-Lactose = D-Galactose + D-Glucose

• Lactose is broken down into one galactose and one glucose in a chemical reaction facilitated by the lactase enzyme

– The lactase enzyme is present in the small intestine

• Once lactose has been broken down into one galactose and one glucose in the small intestine:– The monosaccharides are absorbed into the blood and trafficked to the liver cells for metabolism

+O

HH

Lactose H2O

+O

OHOH

HO

OH

CH2OH

Glucose Galactose

Lactase

O OH

OH

OH

CH2OH

O

OHHO

OH

CH2OH

OO OH

OH

HO

OH

CH2OH

Page 40: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Disaccharide: Lactose

OO

OH

HO

OH

CH2OH

O

OHOH

OH

CH2OH

Galactose Glucose

O

HH

HO

H

Lactose disaccharide

Animation of the breakdown of lactose

An extra alcohol functional group is created on galactose

and glucose

Page 41: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Lactose intolerance:

Individuals who produce less lactase enzyme (in the small intestine)

do not breakdown lactose efficiently

– For a lactose intolerant person, some lactose will pass through the small intestine undigested

• In the large intestine bacteria breakdown the lactose producing lactic acid and gas which cause

cramping, nausea and diarrhea

+O

HH

Lactose H2O

+O

OHOH

HO

OH

CH2OH

Glucose Galactose

Low amount of

LactaseO OH

OH

OH

CH2OH

O

OHHO

OH

CH2OH

OO

OH

HO

OH

CH2OH

Limited conversion of lactose into

monosaccharides

– Causes of reduced amount of lactase enzyme:

• Genetic mutation in the gene that produces the lactase enzyme

• Injuries to intestinal mucosa where the lactase enzyme is produced

OH

Page 42: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Disaccharide: SucroseD-Sucrose = D-Fructose + D-Glucose

• The fructose and glucose units within sucrose are connected via a glycosidic bond

• Sucrose is the sweetest sugar found in fruit and honey– Table sugar is made up of sucrose

• The body cannot store fructose so it must be metabolised by the liver– Some of the fructose is converted into:

• Glucose

• Triacylglycerol (Fat)

Glucose Fructose

Sucrose

https://www.freeimages.com/photo/salt-n-pepper-n-sugar-1555673

Page 43: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Disaccharide: Sucrose

D-Sucrose = D-Fructose + D-Glucose

• Sucrose is broken down into one fructose and one glucose in a chemical reaction facilitated by the sucrase enzyme

– The sucrase enzyme is present in the small intestine

• Once sucrose has been broken down into one fructose and one glucose in the small intestine:– The monosaccharides are absorbed into the blood and trafficked to the liver cells for metabolism

+O

HH

Sucrose H2O

+O

OHOH

HO

OH

CH2OH

Glucose Fructose

SucraseO

OHOH

CH2OH

HO

CH2OH

O

OHHO

OH

CH2OH

O

O

OHHO

OH

CH2OH

HO

CH2OH

Page 44: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Disaccharide: Sucrose

HO

OO

OH

OH

CH2OH

FructoseGlucose

O

HH

HO

H

Sucrose disaccharide

Animation of the breakdown of sucrose

An extra alcohol functional group is created on fructose

and glucose

O

OHHO

OH

CH2OH

HO

CH2OH

Page 45: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Describe the chemical reaction where one

glucose and one fructose connect together to form the

disaccharide sucrose.

Can the glycosidic bond that connects the two

monosaccharides within sucrose be broken? If so how?

Why might it be useful to break sucrose down

into two individual monosaccharide units?

Key concept: Formation and breakage of glycosidic bonds

Page 46: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Attempt Socrative questions: 5 to 7

Google Socrative and go to the student login

Room name:

City name followed by 1 or 2 (e.g. PERTH1)

1 for 1st session of the week and 2 for 2nd session of the week

Page 47: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Part 2: Disaccharides

• Glycosidic bond– A glycosidic bond is formed between two sugar units in a chemical

reaction, allowing two individual sugar units to form one compound (a disaccharide)

– To form a glycosidic bond there is a reaction between two alcohol groups in two different sugar units

– Once a glycosidic bond has formed, an ether functional group is present at the location of the glycosidic bond

• Digestion of dietary carbohydrates– Digestive enzymes facilitate the breakdown of dietary carbohydrates by

cleaving the glycosidic bonds which connect sugar units together– Only monosaccharides can be absorbed by the small intestine into the

blood– Once in the blood, monosaccharides are delivered to specific cell types to

be metabolised into cellular energy (ATP)

Page 48: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Part 2: Disaccharides

• Disaccharide: Maltose– Maltose is made up of two glucose units connect by a glycosidic bond– The maltase enzyme facilitates the breakdown of maltose into two individual

glucose units

• Disaccharide: Lactose– Lactose is made up of one galactose and one glucose connect by a glycosidic

bond– The lactase enzyme facilitates the breakdown of lactose into one galactose and

one glucose– Lactose intolerant individuals produce less lactase enzyme, so they are less

efficient at breaking down lactose during digestion

• Disaccharide: Sucrose– Sucrose is made up of one fructose and one glucose connect by a glycosidic bond– The sucrase enzyme facilitates the breakdown of sucrose into one fructose and

one glucose– Table sugar is made up of sucrose

Page 49: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Part 3: Polysaccharides

• Digestible vs non-digestible polysaccharides

• Polysaccharide: glycogen

Page 50: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Many, many sugar unit compound

https://www.freeimages.com/photo/baked-potatoes-1532388

https://www.freeimages.com/photo/a-leaf-1488203

https://www.freeimages.com/photo/the-bug-1180812

Starch Cellulose Chitin GlycogenGlycogen is an energy storage compound that is found in the liver and muscle

Glycogen is broken down into glucose units at the beginning of a run to provide quick energy generation

Cellulose provides structural support to plants

Chitin is found in the exoskeletons of insects

Potatoes are a starch rich food

Starch is made up of many glucose units which are slowly released into the blood as digestion occurs

Digestible vs non-digestible

polysaccharides

Polysaccharide: A compound made up of 100 to 1 million sugar units is a polysaccharide– Examples: Starch, glycogen, cellulose and chitin

Page 51: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Digestible vs non-digestible

polysaccharides

Polysaccharides are contain many, many monosaccharide units connected via glycosidic linkages

• Distinctive features of different polysaccharides:

– The identity of the monosaccharide monomer within the polysaccharide

– Length of chain varies from few hundred sugar units

up to 1 million sugar units

– Degree of chain branching with the polysaccharide

Many, many sugar unit compound

Page 52: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Digestible vs non-digestible polysaccharidesCELLULOSE

CELLULOSE PASSES THROUGH THE MOUTH, STOMACH AND SMALL

INTESTINE UNDIGESTED

POLYSACCARIDE COMPOSED OF

MANY CONNECTED GLUCOSE UNITS

NO NUTRITIONAL VALUE FROM CELLULOSE AS IT CANNOT BE ABSORBED

BY THE SMALL INTESTINE

After eating a cellulose

containing food

CELLULOSE ENTERS THE LARGE INTESTINE

WHERE IT ASSISTS WITH EXCRETION OF SOLID

WASTE

THE BODY LACKS THE ENZYME REQUIRED TO

BREAKDOWN CELLULOSE INTO INVIDUAL GLUCOSE

UNITS

Definition

Why?

Consequence

Consequence

Page 53: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Digestible vs non-digestible polysaccharides

STARCH

α-AMYLASE ENZYME BREAKS DOWN STARCH INTO MANY GLUCOSE

UNITS

POLYSACCARIDE COMPOSED OF

MANY CONNECTED GLUCOSE UNITS

GLUCOSE UNITS DERIVED FROM STARCH ARE ABSORBED BY THE SMALL INTESTINE

After eating a starch containing food

Definition

Consequence

TRAFFICKED TO OTHER CELL TYPES INCLUDING THE LIVER, BRAIN AND

MUSCLE TO BE METABOLISED INTO

CELLULAR ENERGY (ATP)

Glucose

Page 54: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

DIGESTABLE

POLYSACCHARIDES

POLYSACCHARIDES CONTAIN MANY

GLYCOSIDIC BONDS

SLOW ABSORPTION OF THE MONOSACCHARIDES RELEASED FROM THE

POLYSACCHARIDE DURING DIGESTION

DISACCHARIDES AND

MONOSACCHARIDES

DISACCHARIDES CONTAIN ONE GLYCOSIDIC BOND AND

MONOSACCHARIDES CONTAIN NO GLYCOSIDIC BONDS

FAST ABSORPTION OF MONOSACCHARIDES AND

DISACCHARIDES DURING DIGESTION

MANY GLYCOSIDIC BONDS TO BREAK

WITHIN THE POLYSACCHARIDE

FEW OR NO GLYCOSIDIC

BONDS TO BREAK

SLOW RELEASE OF GLUCOSE INTO THE BLOOD

FAST RELEASE OF GLUCOSE INTO

THE BLOOD, CAUSING A SPIKE

Due to

Due to

Page 55: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Polysaccharide: glycogen

• Glycogen is a polysaccharide consisting of up to

1 million glucose units

– In humans glycogen is stored in the liver and muscle

– When required glycogen is broken down into glucose units which can be metabolised to generate ATP

Page 56: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Polysaccharide: glycogen– Excess glucose in the blood, after digestion of dietary carbohydrates,

results in the production of glycogen (glycogenesis)

• Glycogen functions as a glucose storage component

– A low blood glucose level stimulates the breakdown of glycogen

into individual glucose units (glycogenolysis)

• Glucose units can then be metabolised into cellular energy (ATP)

Glycogen1 million

glucose units

Glycogenesis

Glycogenolysis

ATP generation

from glucose

Glucose storage

in the liver and muscle

Page 57: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Why can humans digest starch but not cellulose?

Why is it necessary to breakdown dietary carbohydrates

into monosaccharides during digestion?

If there is excess glucose after digestion,

what will the excess glucose be used for?

Key concept: digestible vs non-digestible carbohydrates

Page 58: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Attempt Socrative questions: 8 to 10

Google Socrative and go to the student login

Room name:

City name followed by 1 or 2 (e.g. PERTH1)

1 for 1st session of the week and 2 for 2nd session of the week

Page 59: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Part 3: Polysaccharides

• Digestible vs non-digestible polysaccharides– Cellulose cannot be digested by humans, as humans lack the enzyme required

to break the glycosidic bonds present in cellulose– Cellulose provides no nutritional value to humans but it does help with excretion of solid

waste– Starch can be digested by humans, as humans have the α-amylase enzyme required to

break the glycosidic bonds present in starch– The glucose units released from the digestion of starch are trafficked to cells (via the blood) to

generate cellular energy (ATP)– The more glycosidic bonds a sugar contains the slower it is digested– Starch is digested slowly and consequently releases glucose into the blood slowly– Disaccharides and monosaccharides are digested quickly and can cause the blood glucose

level to increase rapidly

• Polysaccharide: glycogen– Glycogen is a polysaccharide consisting of up to 1 million glucose units– Glycogen is stored in the liver and muscle– Glycogen is created from glucose when glucose is in excess (glycogenesis)– Glycogen is broken down into glucose when blood glucose is low (glycogenolysis)

Page 60: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

Readings & Resources• Stoker, HS 2014, General, Organic and Biological Chemistry, 7th edn,

Brooks/Cole, Cengage Learning, Belmont, CA.

• Stoker, HS 2004, General, Organic and Biological Chemistry, 3rd edn, Houghton Mifflin, Boston, MA.

• Timberlake, KC 2014, General, organic, and biological chemistry: structures of life, 4th edn, Pearson, Boston, MA.

• Alberts, B, Johnson, A, Lewis, J, Raff, M, Roberts, K & Walter P 2008, Molecular biology of the cell, 5th edn, Garland Science, New York.

• Berg, JM, Tymoczko, JL & Stryer, L 2012, Biochemistry, 7th edn, W.H. Freeman, New York.

• Dominiczak, MH 2007, Flesh and bones of metabolism, Elsevier Mosby, Edinburgh.

• Tortora, GJ & Derrickson, B 2014, Principles of Anatomy and Physiology, 14th edn, John Wiley & Sons, Hoboken, NJ.

• Tortora, GJ & Grabowski, SR 2003, Principles of Anatomy and Physiology, 10th edn, John Wiley & Sons, New York, NY.

Page 61: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,

© Endeavour College of Natural Health www.endeavour.edu.au 61

Page 62: BIOB111 SN11 Lecture Carbohydrates– Examples: Glucose Two sugar unit compound Glucose Glucose Galactose Glucose Fructose Maltose Lactose Sucrose – Functions: • In a disaccharide,