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In The Name of Gad

In The Name of Gad. Goals of Biochemistry. Chemical Elements in cells : Life depends primarily on which few elements C, O, N, H (99%) + S, P, Na, Cl, Ca, Mg, K + trace amounts various metals. 1- جستجوي ترکيبات يا اجزائ متشكله سلول (جاندار)......

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In The Name of Gad

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  1. In The Name of Gad

  2. Goals of Biochemistry • Chemical Elements in cells : Life depends primarily on which few elements • C, O, N, H (99%) • + S, P, Na, Cl, Ca, Mg, K • + trace amounts various metals 1- جستجوي ترکيبات يا اجزائ متشكله سلول (جاندار)...... 2- شناخت چگونگي واكنشهاي بيوشيميايي در سلول .... تفاوت واکنش هاي بيوشيمائي و شيميائي. • Why these? • 1. Available • 2. Suitable – C, H, O and N have strong tendencies to form covalent bonds -Miler hypothesis

  3. بيومولكولهاي موجود در موجودات آلي Organic Molecules – Four Classes Class Monomer (subunit) Polymer Carbohydrates Sugar Polysaccharides Lipids Fatty Acids Lipids, Phospholipids Proteins Amino Acids Proteins Nucleic Acids Nucleotides (DNA, RNA) Carbohydrates Lipids Nucleic Acids Proteins

  4. Nucleus Nucleolus Rough ER اجزائ تشکیل دهنده سلول Mitochondria Lysosome Smooth ER Golgi Plasma membrane

  5. گروهاي عملكردي در بيومولكولها Biomolecules: Functional Groups هيدروكسيل كربونيل آمين آميد تيول استر آلكن

  6. Carbohydrates 1-کربوهیدراتها 2- انواع کربوهیداتها 3 - مونوساکاریدها (نامگذاری ، فرمول، ایزومر نوری، اپیمر ،انانتیومر،آنومر ،)LوD 3-خواص مونوساکاریدها : گروه کربونیل(اکسیداسیون، اثر بازها ،اسیدها ،مواداحیا کننده، هیروکسیل آمین ،اسید سیانیدریک) گروه هیدروکسیل(پیوند گلیکوزیدی ، تشکیل استر) -مشتقات مونوساکاریدها: 4 قندهای دزاکسی ، قندهای آمین دار 5- الیگو ساکاریدها : دی ساکاریدها (مالتوز، لاکتوز،سلوبیلوز، ساکاروز،تره هالوز) 6- پلی ساکاریدها: همو پلی ساکاریدها(نشاسته، گلیکوژن،دکستران،سلولز،کیتین) هترو پلی ساکاریدها (اسید هیالورونیک ، هپارین، کراتان،درماتان، کنروئتین سولفات)

  7. Photosynthesis: Sun’s energy becomes part of glucose molecule energy ,1% of body weight گلوكز Carbon dioxide Water Chlorophyll GLUCOSE 6 CO2 + 6 H20 + energy (sun) C6H12O6 + 6 O2

  8. Carbohydrates (glucides, Osides…) کربوهیدارت ها،گلوسیدها،اوزیدها،ساکاریدها • Monosaccharides - simple sugars with multiple OH groups. Based on number of carbons (3, 4, 5, 6), a monosaccharide is a triose, tetrose, pentose or hexose. مونوساكاريد • Oligosaccharides - a few monosaccharides covalently linked. (2-7) اوليگوساكاريد -Disaccharides - 2 monosaccharides covalently linked. دي ساكاريد -Trisaccharides - 3 monosaccharides covalently linked. تری ساكاريد • Polysaccharides - polymers consisting of chains of monosaccharide or disaccharide units. ( 10…) پلي ساكاريد

  9. each have the same formulae C3H6O3 Monosaccharides • There are two families of monosaccharides: • Aldose- containing an aldehyde functional group suffix –ose اوز ( Ribose) , Aldotriose….. • Ketose- containing a ketone functional group (suffix -ul ُال ( Ribulose ) , Ketotriose….. ketose aldose -ساختمان خطی- مدل فیشر -ساختمان حلقوی- مدل هاوورث ساختمان قندها

  10. ساختمان خطي مونوساكاريد ها Linear Structure: Monosaccharides Aldoses (e.g., glucose) have an aldehyde group at one end. Ketoses (e.g., fructose) have a keto group, usually at C2. ايزومر عاملي: تفا وت در گروه عامل- 1 2 3 4 5 6 1 2 3 4 5 6

  11. D-ketoses D-aldoses تریوزها-3 4-تتروزها 5-پنتوزها 6-هگزوزها 7-هپتوزها

  12. ايزومر :مونوساكاريد هاMonosaccharides :Isomers The number of isomers is 2n, where n is the number of asymmetric centers. (R- aldose n=m-1 , R- ketose , L-aldose n=m-2, L-ketose n=m-3 , m= number of carbon ) 1- D &L Isomeri 2-(Enantiomers, Racemic )انانتيومر – راسميك 3-Epimerism Isomeri ايزومر اپي مر 4-Anomerism Isomeriايزومر آنومري Definition: Isomer 1-Functional isomers:.ايزومر عاملي 2-Ring isomers:ایزومر حلقه 3-Optical isomers:ایزومر نوری

  13. CHO HO H H OH CH2OH C C مونوساكاريدها D ,L ايزومرMonosaccharides : D ,L Isomers قرار کرفتن گروهOH بر روي آخرين كربن نامتقارن با هم تفاوت دارد.اگر در سمت راست باشد قند از نوع D و اگر در سمت چپ باشد از نوع L است.قندهای مهم از لجاظ بیولوژیک از نوع D هستند.برای نشان دادن جهت انحراف نور از علامت + و- استفاده می شود. CHO CH2OH L-glyceraldehyde Laevo (left) D-glyceraldehyde Dextro (right)

  14. Enantiomers انانتيومرها Monosaccharides :Enantiomers • :A special subset of isomers when 2 sugars differ only in the configuration around All carbon . بر روي تمام كربن هاي نامتقارن با هم تفاوت داردOH,H نحوه قرار گيري گروه

  15. CHO CHO CHO CHO H OH HO H H H OH OH HO H HO HO HO H H H C C C C C C C C C C C C C C C C HO H H H H OH OH OH H OH H OH H H OH OH CH2OH D-galactose D-glucose D-mannose CH2OH D-glucose CH2OH CH2OH اپي مرهاMonosaccharides:Epimers :A special subset of isomers when 2 sugars differ only in the configuration around one carbon. بر روي يكي از كربن هاي نامتقارن با هم تفاوت داردOH,H نحوه قرار گيري گروه D-mannose is a C-2 epimer of D-glucose! D-galactose is a C-4 epimer of D-glucose! NOTE: D-mannose is NOT an epimer of D-galactose b/c configuration about 2 carbons is different.

  16. Ring Structures ساختمان حلقوي :اثبات • 1-Hemiacetal & hemiketal • formation اگر آلدئيد با يك الكل واكنش دهد محصول آن نوعي استال است در حاليكه واكنش مونوساكاريدها با الكل فقط همي استال است H OR R-OH C Hcl R OR استال Acetal 2-Methylation واكنش متيلاسيون glucose must be has 5 molecules methyl. In practical it has 4 molecules .

  17. O O O   O Ring Structures • Monosaccharides with 5 or more carbon atoms in the backbone usually occur in solution as cyclic or ring structures. پيرانوز پيران فورانوز فوران furanose pyran pyranose furan الفا دي گلوكوپيرانوز بتا دي گلوكوپيرانوز

  18. Ring Structures When the ring forms, the –OH on the former carbonyl carbon can have two configurations, given the designations  and . In Haworth projection, the  - OH is down and the  -OH is up. مدل هاوورث These isomers are called anomers, and the carbon atom is referred to as the anomeric carbon atom. ايزومر آنومري كربن آنومريك • The interconversion between  and  forms occurs via the open-chain structure in a reaction called mutarotation. موتوروتاسيون

  19. Fructose forms either • a 6-member pyranose ring, by reaction of the C2 keto group with the OH on C6, or • a 5-member furanose ring, by reaction of the C2 keto group with the OH on C5.

  20. Properties of carbonyl group • Oxidation 1- aldehyde group اسيد گلوكونيك اسيد آلدونيك 2- Aldehyde & Alcoholic group 3- Alcoholic group اسيد گلوكاريك (ساکاریک) اسيد الداريك اسيد گلوكورونيك اسيد اورونيك اسید موسیک Gal

  21. اثرات عوامل احيائ كننده Effects of Reducing Agent: The reducing agent can reduce keto group and aldehyde group to hydroxyl group سوربيتول مانيتول D-Manose D-Glucose & fructose Ribose Ribitol ريبتول Galactose Dolcitol دولسيتول

  22. Effects of diluted alkali : Tautomerization توتومريزاسيون Mannose Effects of Conc Acids: Pentose Furfural فورفورال Hexose Hydroxy metyl Furfural هيدروكسي متيل فورفورال Effects of HCN :اسيد سيانيدريك Production of a new sugar with a addition carbon Effect of Hydroxyl Amine:هيدروكسيل آمين Production of a new sugar with lower a carbon

  23. Reducing Sugars • Monosaccharides are also known as reducing sugars, • Such reactions are used in the analysis of sugars, e.g. Benedict’s Solution RCHO + 2Cu2+ RCO2H + Cu2O (RED) معرف بنديكت

  24. Properties of Hydroxyl Groups • Hydroxy groups are modified in monosaccharides to give a number of important derivatives: • Phosphorylation • Glycosides (elimination of water between anomeric hydroxyl group and hydroxyl of another compound) فسفوريلاسيون گليكوزيدي

  25. Glycosidic Bonds The anomeric hydroxyl and a hydroxyl of another sugar or some other compound can join together, splitting out water to form a glycosidic bond: R-OH + HO-R'R-O-R' + H2O E.g., methanol reacts with the anomeric OH on glucose to form methyl glucoside (methyl-glucopyranose). پيوند گليكوزيدي

  26. Sugar derivatives amino sugar - an amino group substitutes for a hydroxyl on C-2. An example is glucosamine. The amino group may be acetylated, as in N-acetylglucosamine. ان استيل گلوكز آمين الفا دي گلوكز آمين

  27. Sugar derivatives ان –استيل نورامنيك اسيد –اسيدسياليك N-acetylneuraminate (N-acetylneuraminic acid, also called sialic acid) is often found as a terminal residue of oligosaccharide chains of glycoproteins. Sialic acid imparts negative charge to glycoproteins, because its carboxyl group tends to dissociate a proton at physiological pH, as shown here.

  28. Sugar derivatives دزاكسي ريبوز ريبوز Structure of DNA ,RNA NADH ,ATP,…... فوكوزL- Fucose = 6- Deoxy-L- Galactose رامنوز L-Ramnose =6-Deoxy -L- Manose

  29. Oligosaccharides • -2-7 مونوساکارید با پیوندهای گلیکوزیدی به یکدیگر اتصال دارند. • دی ساکارید : • 1- احیائ کننده : مالتوز ، لاکتوز، سلوبیلوز • 2- غیر احیائ کننده: ساکاروز ،تره هالوز • تری ساکارید: مانند رافینوز(گلوکز-گالاکتوز-فروکتوز)

  30. CH2OH CH2OH H2O O O OH OH OH OH HO HO OH OH Disaccharides • Two Monosaccharides are covalently linked to one another by glycosidic bonds that are acid labile, but base resistant. They are also hydrolyzed by specific enzymes. Writing the Structure of Disaccharides 1. the nonreducing end at the left. 2 The ring configuration is indicated by a suffix . ( osyl - ose) اوزيل -اوز 3. The atoms between which glycosidic bonds are formed are indicated by numbers in parentheses between residue designations. ( 1 4) + H مالتوز • α-D-glucopyranosyl-(14)- α-D--glucopyranose.)

  31. Disaccharides: مالتوزMaltose, a cleavage product of starch, is a disaccharide with a(1®4) glycosidic link between the C1 OH & C4 OH of 2 glucoses. It is the a anomer (C1 O points down). سلوبيوز Cellobiose, a product of cellulose breakdown, is the otherwise equivalent b anomer . The b(1®4) glycosidic linkage is represented as a zig-zag, but one glucose is actually flipped over relative to the other. • α-D-glucopyranosyl-(14)- α-D--glucopyranose.) • β-D-glucopyranosyl-(14)- β-D--glucopyranose.)

  32. لاكتوزLactose, milk sugar, is composed of galactose & glucose, with β(14) linkage from the anomeric OH galactose. β-D-galactopyranosyl-(14)- β-D-glucopyranose ساكاروزSucrose, common table sugar, has a glycosidic bond linking the anomeric hydroxyls of glucose & fructose. α-D-glucopyranosyl-(12)- β-D-fructofuranoside.

  33. Disaccharides

  34. Polysaccharides • The most important homopolysaccharides involve D-glucose monomers and are: • Glycogen- main storage polysaccharide of animal cells • Starch (amylose and amylopectin)- main storage polysaccharide of plant cells. • Cellulose- structural polysaccharide of plants • Chitin- major structural material in the exoskeletons of many arthropods and mollusks. (N-Acetyl Glucose Amine )n 1 4 • Inolin (b -D fructofuranose)n 1 2 1-HomoPolysaccharides:هوموپلي ساكاريدها 2-HeteroPolysaccharides:هتروپلي ساكاريدها

  35. -amylose Starchنشاسته: There are two forms of starch آميلوز-1-amylose: D-glucose linked (14) with no branching,20-15 % ,60-600 Glu, • آميلوپكتين-2 amylopectin: D-glucose linked (14) and (16) with branching,80-85% ,600.00, • 24-30 Glc Branching site amylopectin

  36. Glycogen:گليكوژن • Glycogen is comprised of D-glucose monomers linked (14) and (16) Therefore, • it is a highly branched structure. • Glycogen is hydrolyzed by enzymes. located in animal cells. .

  37. Cellulose:سلولز • Cellulose is comprised of D-glucose monomers linked (14). • 300-3000 unit. • Cellulose is hydrolyzed by the enzyme cellulase. • Vertebrates can not hydrolyze cellulose because they lack the enzyme cellulase. Microorgnisms in ruminants do produce cellulase and therefore cattle, sheep, goats, etc utilize cellulose indirectly.

  38. 2-HeteroPolysaccharides گليكوپروتئين ها Proteins conjugated to saccharides lacking a serial repeat unit Glycoproteins and Proteoglycans Glycoproteins Protein >> carbohydrate پروتئو گلايكن ها Proteins conjugated to polysaccharides with serial repeat units Proteoglycans Carbohydrate >> protein گلايكوزوآمينوگلايكن ها موكوپلي ساكاريدها Glycosaminoglycans Mucopolysaccharides Repeat unit HexN and HexUA

  39. Glycoproteins • Oligosaccharides are covalently attached to proteins in one of two ways: • N-linked: CHO to Asn found within the protein sequence Asn-X-Ser(Thr) where X is almost any amino acid (except Pro, Asp or Glu). The CHO is most often GlcNAc and sometimes GalNAc.آسپارژين • O-linked: CHO to Ser or Thr or hydroxylysine or hydroxylproline. The CHO is most often GalNAc. All blood group antigens are oligosaccharides O-linked to both proteins and lipids.سرين –تره اونين • Oligosaccharides that are linked to proteins are generally called carbohydrate moieties

  40. Glycopeptide bonds Protein Asn Glc NAc Type I N-Glycosyl linkage to Asn Protein Ser Glc NAc O-Glycosyl linkage to Ser (Thr) Type II

  41. گليکو ليپيد ها مانند ليپو پلي ساکاريد باکتريها: قند>ليپيد قند+چربي گليکوليپيده (آنتي ژنهاي گروه خوني):ليپيد>قند Blood group antigen O گروه خوني A گروه خوني B گروه خوني

  42. b-1,3 b-1,4 موكوپلي ساكاريدها Glycosaminoglycans GlcUA GlcNAc -استيل گلوكز آمين - اسيد گلوكورونيكN- No sulfate b-1,3 glycosidic linkage اسيد هيالورونيك Hyaluronate

  43. b-1,3 b-1,3 b-1,4 b-1,4 Glycosaminoglycans -استيل گالاكتوز آمين - اسيد يدورونيكN- Dermatan sulfateدرماتان سولفات IdUA GalNAc GalNAc GlcUA كند روتئين سولفاتChondroitin sulfate -استيل گالاكتوز آمين - اسيدگلوكورونيكN-

  44. b-1,4 a-1,4 b-1,3 a-1,4 Glycosaminoglycans -استيل گلوكز آمين - گالاکتوزN- GlcUA GlcNAc Keratan sulfateكراتان سولفات IdUA GlcAmine هپارين Heparin استيل گلوكز آمين - اسيديدورونيك-N

  45. Hemiacetal & hemiketal formation An aldehyde can react with an alcohol to form a hemiacetal. A ketone can react with an alcohol to form a hemiketal.

  46. Cyclization of glucose produces a new asymmetric centerat C1. The 2 stereoisomers are called anomers, a & b. Haworth projections represent the cyclic sugars as having essentially planar rings, with the OH at the anomeric C1: • a(OH below the ring) • b (OH above the ring).

  47. Because of the tetrahedral nature of carbon bonds, pyranose sugars actually assume a "chair" or "boat" configuration, depending on the sugar. The representation above reflects the chair configuration of the glucopyranose ring more accurately than the Haworth projection.

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