Carbohydrates and glycolysis (part 1) notes
Carbohydrates and glycolysis (part 1) notes CHEM 3550
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This page Class Notes was uploaded by Hinal Patel on Wednesday February 17, 2016. The Class Notes belongs to CHEM 3550 at 1 MDSS-SGSLM-Langley AFB Advanced Education in General Dentistry 12 Months taught by Dr. Szymczyna in Winter 2016. Since its upload, it has received 22 views. For similar materials see Introduction to biochemistry in Chemistry at 1 MDSS-SGSLM-Langley AFB Advanced Education in General Dentistry 12 Months.
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Date Created: 02/17/16
Carbohydrates Wednesday February 242016 1222 PM CARBOHYDRAT 0 Chemical and structural differences of sugars 0 The chemical reactions of sugars 0 Disaccharides and polysaccharides 0 Glycoconjugates 0 Monosaccharides are the simplest carbohydrates 0 Monosaccharides They are aldehydes or ketones that contain two or more alcohol groups 0 Smallest monosaccharides are composed ofthree carbons 0 End carbon closest to the most oxidized carbon is 1 0 Monosaccharides exist in many isomeric forms ISOMERS mums 39 39 m 0 O n ly co u nt chiral ca rbo n s fo r m irro r carbonnom no no om CONSTITUTIOJNALISOMERS STEREOISOMEIS H C OH HO C H or In m order of attachment of atoms Atoms are connected 0 antenatal H quot i v quot f quot i quot 0 Epimers have one chiral center that is a Fife o H lZ OH H IIZ OH m OH to CH OH anon 39 39 a cuawghra oihyfcl H ova m I r 39 tereoisomers are mixe c ira s an 0 Dias d h l d ENAN I39IJOMEHS DIAS I ERECDISOMEI39lSI NM Nonwpodmposabln mineill as lsommsmatmiwlmluor mega 0 39 always have more than one chiral i Ci HO C H H C OH quot20quot 93920quot quot10quot quot0quot c 0H 40 c on center UM 0 50quot M cl on u c on T H H quot1233 cl c 0quot quot quot H0H 040 ON on pm nan lt 43 u an Where did we see Laud twig Tang 13x this before 0 The D family of Aldose sugars always pay attention to the 2nd to last carbon H f OH l K I l o Rightgt D 0 Left gt L 0 Chirality 0 Defined by the chiral carbon furthestfrom the oxidized carbon Tuo quotfc quot Carbon 5 is the last chiral carbon furthestfrom o H o H mic H the oxidized carbon C i 2 OH l H g OH HO E H H JF OH l 6 l CHZOH CHZOH CH20H DGlycoraldohydo LGlycoraldohydo DGlucose an aldose an aldose Hemiacetal or hemiketal ll R C 0 Aldehyde Ketone Naming of cyclic sugars o Glucose formsa sixmember ring pyranose since it resembles pyran Fructose will form a fivemember ring Furanose since it resembles furan 002 6crazequot 5 39OH H H 733 x r 1 0 HO 3 OH 2H DGlucose openchain form 6oHQOH R39oH Alcohol f 39 R OH Alcohol Hemiacetal formation in glucose Many common sugars exist in cyclic form 5 and 6membered sugars predominantly adopt cyclic structures in solution gt CH20H 33 H 0 H Anomeric on H HO on Carbon H OH aDGlucopylanose HOH cnzon quota o HAnomeric 62 u H H Carbon BDGlucopyranou Two ways represent ring structures H C1 OH 12 0 OH groups on right side of Fischer diagram I l R C OH39 OH Hemiacetal OH R C OR39 R Hemikelal 0 These reactions occur through nucleophillic attack Alpha or beta designation based upon chirality at anomeric carbon Alpha and beta conformations will interconvert in water The linear conformation is the least dominant species in solution H c UH HO l3 H O Anomeric l4 1 Carbon H CIS OH OH H c5 CHZOH Fischer Haworth OH groups on right side of Fischer diagram end up pointing down in Haworth structure Hemiketal formation in fructose CHEOH o 7 0 HO C H HOCH O CHOOH noon 0 OH 2 L f7quot H C OH HO HO OH CHhOH H C Oll H OH CHOH DFructose ao Fructoturanose uFructofuranose end up pomtlngdown In IIawortn Strucwre Fischer left haworth up Alpha or berta designation is still relaige to the orientation ofthe anomeric OH group Sugars havefunction groups that are susceptible to chemical reactions 0 Can be oxidized or reduced 0 Can be esterified 0 Can be isomerized 0 Can be attached to proteins or lipids Reducing sugars have accessible functional groups that can be oxidized 0 Reaction with Benedict39s solution or Fehlings solution K H i CH20H H C OH 2 H C OH 0 OH Cu Cu gt Cu20 H g H HO T H Ho cl H Ho H H C OH 2039 0 H C OH CH20H CH20H Glucose Sorbitol How can ketoses like fructose get reduced nHydrokaetone CHZOH 00 0 HO C H H uHydroxyaldehyde H C OH l H C OH C O H C OH I ll CHaOH H C CH C OH l l DFructose llO C H HO C H aHydroxy I annual H H c OH H c OH I l co H C OH H c OH I H0 C H CHOH CHVOH l HO C H DGlucose Enedlol l intermediate H O OH H 3 OH CHQOH occurs under basic alkaline conditions DMannose Aldehyde group is interchangeable with ketone group Esterification Reactions OH I O o The methyl group attached makes it OH OCH3 nonreducing R C O R39 An ester 0 ll 0 39 ll R C O P O W l on 0quot A phosphoester GIucose Sphosphate glycolysis glycogenesis and pentose phosphate pathway Esterification Reactions form glycosid es Two types ofglycosides 0 Hemiacetal and hemiketals are reducing sugars H H n l on aVOH R c on Q 0 Acetal ancl ketal are non OH onquot reducing sugars Hemiacetal Acetal 0 quotHemIquot means It can change H R I l V n C OH39 Rquot H gt RCOR39 0H ORquot Hemlkelal Ketal Disaccharides are a type ofglycoside 0 Name disaccharides starting with the lowest number anomeric carbon 0 Alpha if 1st carbon is pointing down in linkage Beta if 1st carbon is pointing up in a bond 0 0 Dehydorgenase redox rxn Lactose or Milk Sugar CHJCH 0 Combination of glucose and galactose in a 3139 4 lt OH gt glycosidic linkage CH C Laclose omen CH OH O HO l 0a OH quot 39 r OH OH 39Lactose Maltose CH9OHO CWOHO 0 An intermediate in starch metabolism Q m 0 Combination of two glucose molecules in a Ho 0 0H Alpha14 glycosidic linkage OH OH uMaltose CHQOH CHOH O O OH OH OH HO O OH OH B Maltose 0 Sucrose or table sugar CHZOH 0 Easily digested by humans 0 0 Combination of a glucose and a fructose in a alpha1 OH beta2 glycosidic linkage HO 0 Start numbering with the structure with less C39s OH CHZOH O 0 OH CHZOH OH Sucrose 0 amylose 0 Linear polymer ofglucose molecules hasa alpha 14 013 Hf 3351 1 glyCOSIdIc linkage 9 0 Lack of branching enables CHeoH CHEOH 01on 34quot formation of a helical structure 0 0 O C d 0 One of the componentsof 0 OH 0 0H g0 0 O04 45 I u c starch OH OH OH 9 0 Cellulose lllo H quotloggm 0 Synthesized by plants 0 4 I H l cu H l39l rllquot cM2 H A D vnnl n M n a nl I k n 1 II CW 0 Hquotom H quotmmquot r39lcuUIIIIIIcIIILIy UCLdLli 394 a H 0 A O IrvX l 0 f a Hquot I up 39 AHA H I LEI AKLJQ I k 0 a mquot 7 9 In age I K j can quotH to H lhoHMIz IquotH no 39 quot 39 x H H H quotH 39 2 to H on 0 Forms long linear structures HIH CH 3 H 0 H quotI s H 9 n 2 H r4 oJx 39 quot P4 4o l n 0t h el Ices HO 39 Hf xxx 39 H 0 OH l1CH3 quot 05 H H H H Amylopectin and Glycogen m 2 Amylopectin plants starch Glycogen animals Predominantly a1 4 linkages I Highly branched a1 6 Technically reducing sugars r 1 6 Iirlaagre Iran11 pair11 Roducing and an 0 Heteroglycans have other groups attached to the sugar CHzOH cnzon 0 OH O 0 0H OH on lecosamInOglvcans Polymers of M NH NH glucosamine or galactosamine derivatives BDGlucosamine BDGalactosamine include a carboxylate or sulfate group cnzoso C00 04on 9 0 o o 63 0 on OH OA M W on 0503 NHSO OH NHCOCH3 quot39Pa39iquot Hyaluronate An anticoagulant Synovial Fluid 0 lecoconiUEates o lecoconiugate a macromolecule that is composed of sugarand another biomolecule protein lipid o lecoorotein a protein that has carbohydrates attached play roles in cellular recognition 0 ProteOglvcan glycosaminoglycans linked to proteins 0 Specific amino acids couple sugars to proteins HOOC HzN GLYCOLYSIS Major Overview of Sugar Metabolism other sugars Glycogen Glycogoncsis C Glycogenolysis Pg 09 d Pertlose pliosphale I h d Glucose Certain pathway amino acids GluooneogeneSis Glycolysis Pyruvale Citric acid cycle Electron transport system ere Fatty acids 0 Sugar Metabolism 0 00000 Glycolysis pathway steps Fates of pyruvate Regulation of glycolysis Gluconeogenesis Glycogen metabolism Pentose phosphate pathway 0 Glucose can be obtained from our diet 1 In 0 Left structure NIinked Asparagine 0 Right structure OIinked Serine and threonine Digestion of starches starts in L U U o quotmquot our mouth through the action l quotMm of the alphaamylase enzyme Cgtltgtltgt randomly cleaves Alpha14 bonds Motrin a mitdem39n Alphaamylase breaks down O O sugars Maltese Glucose Glycolysis occurs in all cell types and converts glucose into pyruvate Overall reaction 2 C Goes from 6 carbon to 3 carbon OH ZADP 2 Pi 2 o tc 21 0 ATP and NADH are high energy Ho OHOH 2 NAD La 2 NADH molecules Glucose Pyruvate STEP 1 hexokinase Specific proteins transport glucose into the cell 01on CH20P03239 Phosphorylation by a kinase traps it o Hexokinase o in the cell 39 0H ATP 0H ADP H IrreverSIble And only forward HO OH HO OH reaction occurs OH OH Glucose Glucose 6phosphate 0 Kinase phosphorylation from ATP G6P STEP 2 Isomerization O cxquot HCOH cc 2 Phosphoglucose Isomerase CH20P03239 H H o H Ho lt H z Lu P 2C 0 2 0 Aldose ketose Isomerization HO H H OH H C 0 quotC H quotquot0 on enlel H 0 H C OH H C OH HO u 39 reverSIble cuzopoaz CH20P03quot Glucose 6phosphate Glucose 6phosphate Fructose 6phosphate Ftuctose 6phosphate GGP openchain form openchain form FGP STEP 3 Committed or Rate Determining Step 203P0H2c cum 23903P0H2C CH20P03 Com mits suga r to the 0 Phosphofructokinase 0 Ho m gt H ADP H glycolySIs fate quot Allosteric 0H Aquot Kev regulatorv enzvme for Fructose 6phosphate F6P FructosWisphosphate 6BP quotquotI glycolysis vom I 39 v o Activated AMP and Fructose 26 bisphosphate Inhibited citrate and ATP 0 STEP 4 CLEAVAGE o c CH20PO3239 Uh d t l y roxyace one CH20P032 HocH phosphate GAP can be further processed DHAP C DHAP cannot H Ho C H Aldolase H C OH H O i H C OH I Glyceraldehyde 3phosphate I39lIC 056 16bisphosphate CH20PO32 F16BP STEP 43 ISOMERIZATION Reversible H Ill H 40 C OH Triose phosphate C DHAP IS Isomerlzed Into GAP isomerase oc 2 H C OH CH20P032quot CHzopo32 Dihydroxyacetone Glyceraldehyde phosphate 3phosphate STEP 5 0 Up until now we have invested 2 Iceral e e 239 c o 31pzosih3 3P 0 ATP molecules e y rogenase H C OH NADquot Pi H C OH NADH H o Gyceradehyde3phosphateIsa CH2 P 3quot quot2 quot 32 high energy molecule GI Id h d 13839 h h I t 273553 5133353 m e Followm g steps harvest the energy GAP STEP 6 first production of ATP 0 op032 0 Glyceraldehyde 13 C Phosplijoglycerate C bisphosphoglycerate has a mase H C OH ADP m H C OH ATP greater phosphoryltransfer CH20P03239 CH20P03239 potential than ATP 1 3Bisphosphoglycerate 3Phosphoglycerate STEP 7 Isomerization o A 0 reversible NC Reversible H C OH Phosphoglycerate mutase H C OPO32 H C OH H H 3Phosphoglycerate 2Phosphoglycerate STEP 8 generation of a molecule with high phosphoryl transfer potential 9 0 0 H20 0P032 High energy enol state 1 0 c Reversible H C OP032 Enolase C Il C OH H H 2Phosphoglycerate Phosphenolpyruvate STEP9 Second Production of ATP 0 Target of regulation ADP o 39 lRREVERSlBLEllll 7 2 H ATP H C PO 39 g o c0 3 E i o C0 o39cc o l l P t K39 g l yruvae Inase I39 H I39 H CH3 Phosphenolpyruvate Pyruvate Pyruvate enolform GLYCOLYSIS SUMMARY Glucose 2 pi 2 ADP 2 NAD 2 pyruvate ZATP 2 NADH 2H 2 H20 3 irreversible steps 2 ATP molecules are invested 4 ATP molecules are produced Control occurs at the irreversible steps especially phosphofructokinase step OOOO Catabolic fates of pyruvate l l 2 unnu Anabolic fates gluconeogenesis mum and alanine synthesis co2 NAD C02 NADH NAD Further Lactic Acid oxidgtion Fermentation Fermentation CltrlC aCld cycle 0 Lactic Acid Fermentation NADH 0 quotO 0 A means of regenerating m NAD V67 NAD In the absense of l oxygen C U s HO c H 0 c io Lactate I 0 Common In muscle and CH3 dehydrogenase CH3 red blood cells Pyruvate Lactate Glucose i 2 Pi 39 ZADP Zlactate i ZA39I39P i 21120 0 Catabolism of Fructose o Fructokinase liver 0 Hexokinase other tissues 39 Both ofthem are primed by ATP Fructose xf umose phosphate Hexrakina muscle and I adipose tissue PFKi FLICl39TlSCf l E lyisplmjspnatiisc Fructose16 bisphusmiale Aldolasc 4 lquot 339 i39539139 l z39ichipi aie ls39uzluul39usa a 3 3 liver GcheraldehydeBphosphate DHAP r Fructoso1phosphatc 7 Fructose i 0 Glyceraldehyde J CSi3939reralleiquotuie IF3S Pyruvate Catabolism of Galactose galactose mm Gaiastctktnaae V Galactose1 phosphate J6 Glucose1 phosphate 3 GIucose1phosphale Phaspl cu glucomutuse 0 Charged into Galactose1 phosphate by ATO 0 Turned into UDPgalactose 0 Epimerized into UDPglucose 0 Used in glycolysis or glycogen storage Pglucose llJvF QII1n e pyrclhcsnhc ryla GlucoseGphosphate glycolysis Catabolism of Glycerol ADP NADH 39 Derived from ATP H NAD Ivl 1 H20quot trIacylglycerol HO C H HO C H oc Glycerol Glycerol quot20H kinase CH20PO33 phosphate 04207032 dehydrogenase Glycerol Glycerol Dihydroxyacetone phosphate phosphate Regulation of Glycolysis o Glycolysis has 3 irreversible steps 0 All three steps are subject to regulation 0 Regulation of hexokinase Inhibited by its product glucose6phosphate 0 Regulation of bvruvate kinase Inhibited byATP and alanine Activated by AMP and Fructose 16 bisphosphate Regulation of Phosphofructokinase 0 Most important control site committed step U HLLIVdLCU lllYHlVllquotllllllUlLCU UYHIIquot Why Because ATP is a high energy signal AMP is a low energy signal A lot of AMP activated 0 Inhibited by citrate in the liver citric acid cycle 0 Fructose 26 bisohosohate Activator of PFK Signal of high fructose6phosphate levels Destruction triggered by epinephrine in liver Production triggered by im high sugar Destruction triggered by glucagon low sugar 39 These are all found in the pancreas 9999 Hormones function via a cyclic AMP cAM P signaltransduction pathway l39 quot quotquot J a c 9 a 3 o 39 9 w 8 90 Q prfg a 0 cAMP produced by adenylate cyclase a 0 Increase in cAMP leads to the activation of Protein Kinase A 0 Glucagon and epinephrine ON 0 Insulin OFF ruction controlled by a single 39iigjfjj apposing functional domains 5 39 SyntheSIs and destruction controlled by a single polypeptide GchaQOTquot with 2 opposingfunctional domains Epinephrine l GLUCOSISCAM nlycolysis inactivequot gx sy Kinase n W 0 no steamer tantra fquot 22 amp239 32339 f A II w Phosphatase o ff92F PFK more active tautMan Lnhn nhgm rI uswa W PI IUIPI39I J Phosphopwteln Q P39 phosphatase I Insulin
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