Transcript of Carbohydrates of Physiologic Significance CARBOHYDRATES ARE ALDEHYDE OR KETONE DERIVATIVES OF...
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- Carbohydrates of Physiologic Significance CARBOHYDRATES ARE
ALDEHYDE OR KETONE DERIVATIVES OF POLYHYDRIC ALCOHOLS (1)
Monosaccharides are those carbohydrates that cannot be hydrolyzed
into simpler carbohydrates: They may be classified as trioses,
tetroses, pentoses, hexoses, or heptoses, depending upon the number
of carbon atoms; and as aldoses or ketoses depending upon whether
they have an aldehyde or ketone group. Examples are listed in Table
131. (2) Disaccharides are condensation products of two
monosaccharide units. Examples are maltose and sucrose. (3)
Oligosaccharides are condensation products of two to ten
monosaccharides; maltotriose* is an example. (4) Polysaccharides
are condensation products of more than ten monosaccharide units;
examples are the starches and dextrins, which may be linear or
branched polymers. Polysaccharides are sometimes classified as
hexosans or pentosans, depending upon the identity of the
constituent monosaccharides
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- Anomers
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- Epimerisation
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- Important Disaccharides
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- starch
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- Glycosaminoglycans (mucopolysaccharides) are complex
carbohydrates characterized by their content of amino sugars and
uronic acids. When these chains are attached to a protein molecule,
the result is a proteoglycan. Proteoglycans provide the ground or
packing substance of connective tissues.
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- Structure of proteoglycan from cartilage
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- Structures of A, B,and O oligosaccharide antigen
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- Carbohydrates Can Be Linked to Proteins Through Asparagine
(N-Linked) or Through Serine or Threonine (O- Linked) Residues
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- What are these moleculs ?
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- Lipids of Physiologic Significance (1) relatively insoluble in
water and (2) soluble in nonpolar solvents such as ether and
chloroform.
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- LIPIDS ARE CLASSIFIED AS SIMPLE OR COMPLEX
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- Fatty Acids Are Named After Corresponding Hydrocarbons
Saturated Fatty Acids Contain No Double Bonds Unsaturated Fatty
Acids Contain One or More Double Bonds Fatty acids may be further
subdivided as follows: (1) Monounsaturated (monoethenoid,
monoenoic) acids, containing one double bond. (2) Polyunsaturated
(polyethenoid, polyenoic) acids, containing two or more double
bonds. ). (3) Eicosanoids: These compounds, derived from eicosa-
(20-carbon) polyenoic fatty acids, comprise the prostanoids,
leukotrienes (LTs), and lipoxins (LXs). Prostanoids include
prostaglandins (PGs), prostacyclins (PGIs), and thromboxanes (TXs
).
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- The General Structure of Fatty Acids The general structure of a
fatty acid is a long hydrocarbon chain with a carboxyl group on
carbon 1 (C1). The general structure of a fatty acid is a long
hydrocarbon chain with a carboxyl group on carbon 1 (C1).
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- A fatty acid (Palmitate 16:0) Hydrophilic carboxylate head
Hydrophobic hydrocarbon tail
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- Space Filled Models of FFAs
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- Common unsaturated fatty acids
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- -3 (n-3) unsaturated fatty acids EPA 20:5 (all cis)
5,8,11,14,17 DHA 22:6 (all cis) 4,7,10,13,16,19 ALA 18:3 (all cis)
9,12,15 alpha-linolenic acids
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- BIOACTIVE LIPIDS: MEMBRANE SPHINGOLIPIDS and GANGLIOSIDES
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- Triacylglycerides and Phospholipids
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- Saturated fatty acid ( sn-1 position) Unsaturated fatty acid
(sn-2 position) Differences in the length and degree of saturation
of fatty acids affect their ability to pack & hence the
fluidity of the bilayer Choline head-group Polar Nonpolar
Phosphatidylcholine
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- Phospholipid Structure CH 2 O P O O O CH CH 2 OO C O C O
Phosphate Glycerol (a) Structural formula (b) Space-filling model
Fatty acids (c) Phospholipid symbol Hydrophobic tails Hydrophilic
head Hydrophobic tails Hydrophilic head CH 2 Choline + N(CH 3 )
3
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- The Lipid Bilayer Tails (hydrophobic) Head (hydrophilic)
Hydrophobic tails Hydrophilic heads bilayer
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- Lipid Bilayer (Double Membrane) Hydrophilic head WATER
Hydrophobic tail The phospholipid bilayer is the basic structures
of biomembranes
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- What is this phospholipids name? a s
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- After PI is phosphorylated to PIP 2, cleavage via Phospholipase
C yields diacylglycerol (and IP 3 ). Phosphatidyl inositol signal
cascades may lead to release of arachidonate.
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- plasmalogens
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- Structure of a ceramide (N-acylsphingosine) Structure of
sphingomyelin Sphingosine
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- Four major phospholipids in mammalian cell membranes
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- (or galactosylceramide)
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- Structures of common sphingolipids: Gangliosides are just
cerebrosides with NANA (sialic acid) attached!
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- Gangliosides Gangliosides are the most complex sphingolipids.
These are carbohydrate-rich sphingolipids that contain at least one
acidic sugar. Ganliosides are synthesized by the ordered, step-wise
addition of sugar residues to ceramide. Synthesis of these complex
lipids requires activated sugars (e.g. UDP-glucose, UDP-galactose,
UDP-N-acetylneuraminate) This is just one example, more than 60
different gangliosides have been characterized. glucose (Glc),
galactose (Gal), N-acetylgalactosamine (GalNAc),
N-Acetylneuraminate (NAN)
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- What is these ?
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- EICOSANOIDS ARE 20-CARBON LIPIDS THAT ACT LOCALLY TO STIMULATE
A VARIETY OF PROCESSES Thromboxanes: produced by platelets; act in
formation of blood clots & reduction of blood flow at the site
of a clot Prostaglandin E 1 O OH CH 3 CO 2 - Prostaglandins: act
through cAMP to stimulate contraction of smooth muscle, affect
blood flow, elevate body temperature, or cause inflamation &
pain Leukotrienes: induce contraction of muscle lining airways to
the lungs. I wont expect you to remember these structures. O CH 3
CO 2 - O OH CH 3 CO 2 - O Thromboxane A 2 Leukotriene A 4
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- MAMMALIAN CELLS SYNTHESIZE EICOSANOIDS FROM ARACHIDONIC ACID
Arachidonic acid is released by breakdown of phospholipids in
response to cell damage or hormonal stimuli. phospholipids
containing arachidonic acid other eicosanoids arachidonate (20:4)
CO 2 - prostaglandin G 2 CO 2 - O O OOH prostaglandin H 2 CO 2 - O
O OH cyclooxygenase aspirin, ibuprofin cyclooxygenase 2 O 2 X
stimulus phospholipase A 2 lysophospholipid H2OH2O Mammals have two
isozymes of cyclooxygenase -- COX-1 & COX-2. The prostaglandins
produced by COX-1 participate in house-keeping functions such as
secretion of gastric mucin; those produced by COX-2 play roles in
inflamation. Aspirin, ibuprofin and acetaminophen (nonsteroidal
anti-inflamatory drugs, NSAIDS) block prostaglandin synthesis by
inhibiting cyclooxygenase.
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- Figure 5-18 Page 155 Size and Compositions of the Lipoproteins
Protein Triglyceride Chylomicron Percent ChylomicronLDLVLDLHDL 100
0 20 40 60 80 Cholesterol Phospholipid Protein Phospholipid
Cholesterol Triglyceride VLDL HDL LDL
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- HDL-PON LDL OX-LDL Plaque Macrophage Inactive products
Up-regulated by light ethanol Down-regulated by heavy ethanol Foam
Cell PON & CAD Status PON & CAD Status
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