Basic Building Blocks of CellsCourse 1 / Lecture 119

vladimira.kvasnicova@lf3.cuni.czDepartment of biochemistry – the 4th floor

office 411

Biogenic elements

= elements essential for structure and function oforganisms

macrobiogenic elements: C O H N Ca P S Na Cl K Mg

• over 0,005 % of body mass

• recommended daily intake over 100 mg

• blood concentration more than micromolar

microbiogenic (trace) elements Fe Cu Zn Se F I Co Cr Mn Mo Si V

• less than 0,005 % of body mass

• recommended daily intake less than 100 mg

• blood concentration: micromolar or lower

Chemical composition of human body(mass %)

60% water (2/3 intracellular, 1/3 extracellular)

18% proteins, peptides, amino acids

15% lipids (mainly triacylglycerols of fatty tissue)

1% saccharides (poly- and monosaccharides)

1% nucleic acids, nucleotides

5% mineral substances

Chemical composition of cells

1. 60 mass% - water

polar solvent, most of chemical reactions in a human body take

place in aqueous solutions

2. 35 mass% - organic compounds

a) high molecular weight (proteins, nucleic acids, glycogen)

b) low molecular weight (glucose, lipids, amino acids, metabolic

intermediates – e.g. organic acids derivatives)

3. 5 mass% - inorganic compounds

xlipid dropletstriacylglycerol

xmicelles, bilayersphospholipid

aggregates

C-C bondsterpenesisoprene

glycosidic bondspolysaccharidesmonosaccharide

phosphodiester b.nucleic acidsnucleotide (4)

peptide bondsproteinsamino acid (21)

bonds(covalent)

biopolymers(macromolecules)

monomer(basic unit)

Organic building blocks of cells

http://en.wikipedia.org/wiki/Lipid

This lecture concentrates on

structure, properties and functions of

• saccharides

• lipids

• nucleotides

individual lectures:

� Structure of proteins (124)

� Structure of nucleic acids (132)

� Structure and function of membranes (137)

Saccharides(= carbohydrates)

• monosaccharides, oligosaccharides, polysaccharides

• polyhydroxyaldehydes or polyhydroxyketones

• aldoses /ketoses

• linear or cyclic monosaccharides

• linear or branched polysaccharides (= glycans)

• include chiral carbon(s) → optical isomerism

• -OH, -CHO can be oxidized to –COOH

• - CHO can be reduced to -OH

• low-molecular sacharides are water soluble and sweet

• energy for cells, structural and signal functions

Saccharides(carbohydrates, glycides)

= polyhydroxyaldehydesor

polyhydroxyketonesD-glucose D-fructose

deoxysaccharides

2-deoxy-D-ribose

amino saccharides

D-glucose amine

The figures have been adopted from Harper´s Biochemistry

NH2

GLUCOSE – central role

The figures have been adopted from Harper´s Biochemistry a z http://www.vuw.ac.nz/staff/paul_teesdale-spittle/organic/chiral_web/images/fig1_5d.gif (April 2007)

chiral carbon

The figure is found at http://www.nmc.edu/~koverbaugh/bio115/Image14.gif (October 2007)

O-glycosidic bond

GLYCOGEN (Glc)n

The figure is found at http://students.ou.edu/R/Ben.A.Rodriguez-1/glycogen.gif (October 2007)

nonreducing end reducing end

OH

CELLULOSE

ββββ-Glc(1→4)Glc

The figures are found at http://web.chemistry.gatech.edu/~williams/bCourse_Information/6521/carbo/glu/cellulose_int_2.jpghttp://www.kjemi.uio.no/14_skole/modul/Evina_organisk/Org_K3fig14_cellulose.JPG (October 2007)

Lipids= group of biological molecules that are

insoluble in aqueous solutions

(they are hydrophobic, lipophilic - nonpolar structures predominate in their molecules - soluble in nonpolar solvents

• structural components of biological membranes

• energy reserves, predominantly in the form of

triacylglycerols (TAG = neutral fat)

• excellent mechanical and thermal insulators

• biologically active compounds

(vitamins, hormones, bile acids, visual pigment)

adopted from: J.Koolman, K.H.Röhm / Color Atlas of Biochemistry, 2nd edition, Thieme 2005

Lipids

Structural components of lipids

• alcohols� glycerol (a)

� sfingosine (b)

� cholesterol (c)

� inositol (d)

• long chain monocarboxylic acids(= fatty acids)

The figures are adopted from http://en.wikipedia.org (April 2007)

a) b)

c) d)

The figure was adopted from: J.Koolman, K.H.Röhm / Color Atlas of Biochemistry, 2nd edition, Thieme 2005

Fatty acids found in lipids mostly contain even number of carbons and cis double bonds.

The figure was adopted from http://en.wikipedia.org/wiki/Fatty_acid (April 2007)

Double bond is rigid, it affect

a spatial structure of unsaturated

acids

The figure is found at http://courses.cm.utexas.edu/archive/Spring2002/CH339K/Robertus/overheads-2/ch11_lipid-struct.jpg(Jan 2007)

Structure of lipids

individual lecturefatty acids are

bound to glycerol by ester bonds

The figure was adopted from: J.Koolman, K.H.Röhm / Color Atlas of Biochemistry, 2nd edition, Thieme 2005

The figure is found at http://courses.cm.utexas.edu/archive/Spring2002/CH339K/Robertus/overheads-2/ch11_cholesterol.jpg (Jan 2007)

squalene(C 30 = triterpene)

ISOPRENOIDS

2-methylbuta-1,3-diene

= isoprene

(polyisoprene)

Naming isoprenoids:

• monoterpenes (C10) 2 x isoprene

• sesquiterpenes (C15) 3 x isoprene

• diterpenes (C20) 4 x isoprene

• triterpenes (C30) 6 x isoprene

• tetraterpenes (C40) 8 x isoprene

� isoprenes are bound either „head to tail“ or „tail to tail“

� terpenes have different degree of unsaturation

� and variety of functional groups

Nucleotides

= heterocyclic N-containing base (pyrimidine or purine)

+ sugar (pentose) + phosphoric acid(s)

UMP, UDP, UTPuridine mono-di-tri phosphate

uridineuracil

TMP, TDP, TTPthymidine mono-di-tri phosphate

thymidinethymine

CMP, CDP, CTPcytidine mono-di-tri phosphate

cytidinecytosine

GMP, GDP, GTPguanosine mono-di-tri phosphate

guanosineguanine

AMP, ADP, ATPadenosine mono-di-tri phosphate

adenosineadenine

abbreviationnucleotidenucleoside(base + sugar)

base

The figure was adopted from Devlin, T. M. (editor): Textbook of Biochemistry with Clinical Correlations, 4th ed. Wiley-Liss, Inc., New York, 1997. ISBN 0-471-15451-2

PURINE BASES

purine

The figure was adopted from Devlin, T. M. (editor): Textbook of Biochemistry with Clinical Correlations, 4th ed. Wiley-Liss, Inc., New York, 1997. ISBN 0-471-15451-2

PYRIMIDINE BASES

pyrimidine

The figure was adopted from Devlin, T. M. (editor): Textbook of Biochemistry with Clinical Correlations, 4th ed. Wiley-Liss, Inc., New York, 1997. ISBN 0-471-15451-2

ribonucleoside deoxyribonucleoside

N-glycosidic bond

The figure was adopted from Devlin, T. M. (editor): Textbook of Biochemistry with Clinical Correlations, 4th ed. Wiley-Liss, Inc., New York, 1997. ISBN 0-471-15451-2

ribonucleosides deoxyribonucleoside

Obrázek převzat z http://www.thebestlinks.com/images/f/f5/ATP.png (říjen 2007)

N-glycosidicbond

Adenosine triphosphate(ATP)

ribose

ester bond

anhydride bonds

Recommended literature

http://www.megabooks.cz/kontakty/