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BASIC CELL BIOLOGY I CHEMISTRY of LIFE BIOPOLYMERS BIOPOLYMERS Lipids Polysaccharides Proteins Nucleic acids LIPIDS The structure of lipids Lecture 5 O C H2 C HC OH HO OH O C H2 C OH HO Glicerol 16 – 20 C atoms long fatty acid Lecture 5 The structure of lipids O C H2C O O C HC O O C H2C O Hydrophilic part Hydrophobic part The structure of lipids Saturated fatty acids (e.g., 18 C – stearinic acid). Unsaturated fatty acids with one double bond (e.g., 18 C – oleinic acid). Polyunsaturated fatty acids with more than one double bond. Lecture 5 The structure of lipids Lecture 5 The structure of lipids Lecture 5 The structure of lipids Lecture 5 Hydrophilic part The structure of lipidtriglyceride depicted in the spacefilling model Hydrophobic part Lecture 5 The structure of lipids O H2 C O HO P O OH O Phospholipids C O C HC O CH2 The phosphate group enhances the hydrophylic properties The structure of lipids Lecture 5 Hydrophilic part Schematic representation of the phpspholipid’s structure Hydrophobic part The structure of lipids Micelle, hydrophobic interactions Lecture 5 The structure of lipids Phospholipid bilayer Lecture 5 The structure of lipids Vesicle surrounded by the bilayer Lecture 5 Lecture 5 The structure of lipids CH 3 H O CH 2 CH 2 Choline N + CH 3 H 3C Phosphatidylcholine = lecitn Emulgator, egg yolk, bile, plant oils Lecture 5 The structure of lipids CH 3 H 3C CH 3 CH 3 CH 3 Lecture 5 The structure of lipids CHOLESTEROL The structure of lipids Lecture 5 Hormones POLYSACCHARIDES Lecture 5 Tautomerisation of the carbohydrates 6 CH 2OH O 1 H 4 HO OH H HO H HO H O H OH OH O H OH OH OH H 1 OH OH H H OH a-D-glycopyranose H H OH 6 CH 2OH H 6 H OH D - glucose 4 HO O H OH H H OH OH 1 H b-D-glycopyranose Tautomerisation of the carbohydrates 6 CH OH HOH 2 5 H 4 HO OH O 1 H O H HO H OH H H 2H OH a-D-ribofuranose OH 2 CH 2OH OH H 1 b-D-fructofuranose H H 2H 1 OH OH 2C CH 2OH O CH 2OH O 3 6 H 2 H3 OH a-D-glycopyranose 5 Lecture 5 3 OH 1 OH H a-D-2-deoxyribofuranose 5 C atoms + O atom = pyranose; 4 C atoms + O atoms = furanose (riboses, fructose) Lecture 5 Disaccharides Glucose a-D-glycopiranose Fructose b-D-fructofuranose 6 CH 2OH O H 4 HO 6 OH H H OH H 1 OH OH H O H 2C 1H OH Condensation - H2O CH 2OH O H H OH Lecture 5 Disaccharides 6 CH OH 2 O H HO OH H H OH OH H 1 6 O OH O H 2C 1 H CH 2OH H H OH Sucrose, been or cane sugar (a-D-glycopyranosyl - b - D-fructofuranoside) Lecture 5 Disaccharides Galactose Glucose b-D-galactopyranose a-D-glycopyranose CH 2OH CH 2OH O HO H OH H H OH O H OH HO H OH H H OH Condensation - H2O H OH 5. LEKCIJA Disaharīdi CH 2OH CH 2OH O HO H OH H H OH O H H O OH H H OH H OH Lactose, milk sugar (1, 4 -O- b-D-galactopyranosyl - a - Dglycopyranoside) Trisaccharides Lecture 5 Raffinose Sucrose Melibiose CH 2 CH 2OH O HO H OH H H H OH Galactose O O H HO OH H H OH OH H OH O CH 2OH O H H H 2C H OH Glucose Fructose ca. 5% in been sugar (b-D-fructofuranosyl - O - a - Dgalactopyranosyl- (1- 6) - a - D-glycopiranoside) Stucture of polysaccharides Lecture 5 6 CH 2OH O H 4 HO OH H H OH H 1 OH a-Dglycopyranose O H HO CH 2OH CH 2OH CH 2OH O H H OH OH OH OH O O OH OH Amylose O H n poly (1,4-O– a-D-glycopyranoside) OH Stucture of polysaccharides 6 CH 2OH H 4 HO Lecture 5 O H OH H H OH OH 1 H b-Dglycopiranose O OH H OH O O O HO CH 2OH CH 2OH CH 2OH O OH OH OH OH Cellulose n poly (1,4-O– b-D-glycopiranoside) OH Stucture of polysaccharides Lecture 5 CH 2OH O HO OH OH CH 3 HN O 2-aminoacetyl-b-D-glycopiranose O OH O O O HO CH 2OH CH 2OH CH 2OH H CH 3 HN O O OH OH CH 3 HN O Chitin OH CH 3 HN n O poly(1,4-O-2-aminoacetyl-b-D-glycopiranoside) Stucture of polysaccharides CH 2OH CH 2OH O H HO Lecture 5 OH H H OH O H H HO OH H H OH O O CH 2OH H CH 2OH H 2C O O H H H OH H H 2C O H O HO H H OH H CH 2OH O H H HO H OH H O H O O HO H O O H HO H OH H H HO H OH Lentinan, poly b-glucan from shiitake mushrooms [Lentinula edodes, Berk (Sharp)] Immunostimulator, anti-cancer drug H PROTEINS Lecture 5 Polypeptide chain O H2N CH C H OH CH2 N H H2 C H C O H C CH2 CH2 Cisteine NH C H2 N N CH C OH SH O H CH2 OH NH + NH2 Arginine Tryptophan Condensation - H2O Lecture 5 Peptide chain Peptide bonds N-terminus O H H2N CH C N CH2 C H H2 C O C CH2 SH H CH2 C-terminus O N CH C CH2 NH C H2 N OH NH + NH2 Tripeptide RCW Protein structure Lecture 5 Amino acids in the protein molecule are connected by peptide bonds 20 amino acids cam make 20n combinations within a polypeptide, where n = the length of polypeptide. Protein molecules are usually made from 100 – 500 amino acid residues. Protein structure Lecture 5 Hydrophobic interactions Hydrogen bonds Disulphide bridge Ionic bonds Polypeptid e chain Lecture 5 Protein structure Levels of the structural organisation of the proteins Protein structure Lecture 5 Chapherones –proteins, which help the other, newly sythesised proteins to fold correctly. Protein structure Lecture 5 GLYCOPROTEINS, LIPOPROTEINS –proteins with saide chains made from carbohydrates or lipids Protein functions Proteīn types Structural proteins Functions Mehanic Storage proteins Amino acid storage Transport proteins Transportation of substances Signaling, coordination Hormones Receptors Contractile proteins Defense proteins Enzymes Response Movement Distinction among self and non-self; defense Catalysis of chemical reactions Lecture 5 Examples Collagen, ellastin, keratin Ovalbumin, casein, seed proteins Hemoglobin, membrane proteins Insulin, peptide hormones Membrane proteins Actin, myosine Immunoglobuline, complement Catalases, ligases, isomerases NUCLEIC ACIDS Formation of the phosphodiester bond Lecture 5 NH 2 C HO O HC 5 P HC C O 5 N 1 CH 2 O HC CH 1 3 2 CH CH free 3’-hydroxyl group at the 3-rd atom of ribose OH HO P O OH P O O + O H N HO O N OH b O P O a C C NH HC O 5 CH 2 9 N O HC C 1 N C NH 2 CH 1 3 CH CH OH H Nucleoside triphosphate Formation of the phosphodiester bond Lecture 5 NH 2 C O HO P O 5 5’-end O HC N HC C N CH 2 O HC CH 3 CH new bond O CH O O H N O P HO O HO P OH O O P OH + OH pyrophosphate CH 2 N O HC 3 C NH C C HC 5 O C N NH 2 CH CH CH OH H 3’-end DNA synthesis Lecture 5 DNA structure 5’-phosphate 3’-hydroxyl Lecture 5 DNA structure Lecture 5 (minor grove) (major grove) 3’ 5’ 20 Å 3’ 5’ Base pair Helical turn - 10,5 b.p, 34 angstroms (Å) DNA structure Lecture 5 DNA structure Rosalind Franclin Lecture 5 Moriss Willkins DNA structure Lecture 5 DNA structure James Watson Lecture 5 Francis Crick DNA structure Lecture 5 DNA structure Lecture 5 DNA superspiralisation Lecture 5 Plectonemic superspiralisation; plasmid DNA DNA superspiralisation Lecture 5 Plectonemic superspiralisation; plasmid DNA DNA superspiralisation Lecture 5 Thoroid superspiralisation in the structure of histones DNA superspiralisation Lecture 5 Thoroid superspiralisation in the structure of histones DNA superspiralisation Lecture 5 Thoroid superspiralisation in the structure of histones Folding of RNA Structure of loops and hairpins Lecture 5 Folding of RNA Structure of the t-RNA molecule