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Biochemistry Biosynthetic and Energy Metabolism and Its Regulation

by: Michael Reilly

Biochemistry Biosynthetic and Energy Metabolism and Its Regulation CHEM 153C

Marketplace > University of California - Los Angeles > Chemistry > CHEM 153C > Biochemistry Biosynthetic and Energy Metabolism and Its Regulation
Michael Reilly
GPA 3.71


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Class Notes
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This 20 page Class Notes was uploaded by Michael Reilly on Friday September 4, 2015. The Class Notes belongs to CHEM 153C at University of California - Los Angeles taught by Staff in Fall. Since its upload, it has received 116 views. For similar materials see /class/178004/chem-153c-university-of-california-los-angeles in Chemistry at University of California - Los Angeles.


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Date Created: 09/04/15
Products of Amino Acid Breakdown Metabolic Breakdown of Individual Amino Acids Glucogenic Ketogenic Pyruvate Acetyl CoA 10 a Ketoglutarate Acetoacetate Succinyl CoA Citric Acid Cycle Intermediates Fumme OIquot Oxaloacetate their Precursors Amino Acid Catabolism m Aceifcmmc Animals cannot carryout m synthesis of precursors of gluconeogenesis from u W acetyICoA or acetoacetate mm m f citIn mute ism mama 92 0 Succinyllc A Lamaum quot1 Conversion of Pyruvate and Oxaloacetate to PEP Gluconeogenesis ATP ADPP 0 COOH 0 H30gCOOH 4 in Degradation to Pyruvate 002 p m Pymde Cninytfsz O C COOH Oxaloacetate Alanine Cysteine Glycine GTP GDPCO2 Serine and Threonine C OOH f P ng PEP H200700039 rrrrrrrrrrrrrrrrrrrrr 7 Glucose quotGluconeoqenesisquot OCiCOOH 4 carboxykmasz Phosphoenolpyruvate Oxaloacetate PEP NADH H NAD l l g H l l v a l l m a nArnino vkewbuiyrve U Threanim Alanine mm Nu cm mvH nmylacm Cysteine mummwL mq Glynn GI ycu ne quot 5 V 3 quotV Serl quote mc f cuo c z b Ccm HC CDD h m M m T reom quote 0 Fuanglummm Dams mummu a am soquot or sax Nquot Hqcicr 000 NH ll 0 Pymvne fHS H3N COO H uKG Glu A Iann 2 A minufran sfzr39ase Al uni n2 Cysteine Ca39l39abolism Various Roules CHZSH H20 SCN O H3N COO 4 HQC g COO39 l Cysteine P ymvafe 5 everal Pufhways Glycine gt Serine Serine Hydroxymefhyl Transferase Alanine Ca39l39abolism H30 C 000 Pymvafe Glycine Ca39l39abollsm HCOU quotCH2quot H20 PLP Threonine gt H C E H l a p Glycine N CH3 H Threonine and Serine Serine Formation of GlycinePLP Schiff Base Lys Enzyme B H fume B H ID COO39 sz l HEN C COO E 6 H P I 0 Trmsiminalionquot P I Ki CHa Glycine quotll CH3 H Enzyme PLP Glycine PLP Schiff Base Schiff Base Forma on of Kefimine Lwibxzwer Lysila zymran39 Lyr lzwnnEll39 H T 000 Hi rcoo H H No H c H a p R p H H H CH H Formafion of Serine 0H2 EnzymerPLP H20 THF Threonine gt Serine H H quotzVquot 5 chrlcr crcocr 9H3 W H H H Senna Hydroxymefhy Transferase H HJH 00 HJNichOU a d U PLP and 6 6 Bond Cleavage H Tvmwsummnmu p Th39eonine N 0H w W H H EnzymePL Th39eoninePLP Schiff Base Schiff Base Formafion of Threonine PLP Schiff Base Ly ialzyme E Forma on of Kefimine m mmmr CoAisH WWW an MD NADH H O H ccocr o S g H 4 H39E39CO T HJC C HJO g SCOA we H H mo H AXenyvz uamwgme 0 FYI Acetadehyde AcetyLCoA H OH H OH H H NADHH NAD o H c lt H 00H 70H 3 H 4mm 3 2 DEHudmgmase Acetadehyde Emmo Conversion of Acemldehyde f0 Acefyl CoA Fonnafion of Serine summary Serine Hydmxymerhy Transferase Lw E39Kyme w 0H2 EnzwerPLP 00007 H20 THF I 2 5 CHon Hr rcoo HJN C COO39 naming PKGw 0H2 H20 W H P 6 gt4 serine Serine Wanquot quotH39 cm H Source of M APO Mafhygfg Iatrahydmfdan N5 AF Mefhylene Tefr ahydr ofolafe 2 Glycine Cleavage Sysfem lycine Decarbaxylase Mulfienzyme Complex H H OF lycine Syn mse reverse direcl ion o H H 50039 o o l l l H m c HicHicHrcH OH quot a u lam ale NAD NADHNH 002 H HlN COU THF H mama 025 V395 smm Glyclne mmLMEMEHHHF Glycine Cleavage System analogous to pyramre dehydmyenase campex Forma on Of Glycine PLP Schiff Base 39 PPr39o39rein PLPdependen l glycine decarboxyase H Protein lipoamidecon l aining profein sum 13 Wilmer 04 TVanslmmanan 39 TPr ofein THFr equir ing enzyme l W CH 39 LPr ofein NADdependen FAD 6Wquot l CH3 l 3 requiring d 39hydr39oipoyl dehydrogenase H20 buyquot 4 p SH EKHHM Decarboxylafion and Transfer of 1 Carbon Unif Fonnafion of N5 NW Mefhylene THF NAD NADH H E39THF 4 E mm W5 SH EHltsichN H2 AP NwrMeihyi eneiTH F N5 Alla Methylene Tefrahydrofolafe CH2 H 0039 K0 f H 10 c NicHicHzicHer OH H a u mm me Formafion of Serine Lys Euzyma39EH 0H Enzymepr T Elimination of Wafer from Serine Serine Dehydra fuse Serine Dehydrafase Forma on of Serine PLP Schiff Base 1quot N CH N OH H H Serine Dehydrafase Forma on of Aminoacr ylafe OH Hchcoo H20 m H H b C Wj 5 g 7 er 20 9 000 p p NH2 Non Enzymatic Step Conversion of Aminoacrylafe f0 Pyruvafe H20 HH 0 Hacrcrcoo Hiciaim CT HHZ mnminu M quotwka Pyruvave N 0H B 0H Aminoacr39ylate mimacrvlm Imine H H Summary HTmor THmamnz gt k543i 5H1 H10 m P E Z Degradation 1390 Oxaloace l a39l39e BMW 1 EH H Asparagine and Asparfafe Serine gt Pyruvate Asparagine gt Asparfafe gt Oxaloacefafe o H20 NH H20CNH2 chicoo KG 0 HaNQCOCK AL H chicoo Haw coo 06 o hum g mmqnm Awnnrmhmn Asparagine Asparme Oxaloaoetate Degradation To uKe roglu39rar a re Arginine Glufamafe Glufamine Hisfidine and Pr oline Glutamate and Glutamine Catabolism mman o NH2 c 900 N01 Argmne CH OH 2 H20 NH i 2 mNrbooor H 252007 Wii m Ho l Mquot Q a l a i 1 Glutamate5 H mm H 1 Wm W O Semialdehyde W Glmam m U N KG a No meow 1 by EH11 HaNrbrOOC Mm HaNiliicoU 5Wst H 00039 r H Amwmn mw H coo goo ryml39ms CH CH r m1 W F 1 0 2 NAD H20 NADH NHA Omnhme quotIrmaquot Carboxylm HaNr rCOU 05400 quotWWW prw H H emmwemmgmm 000 Glutamate It 1 Glutamate uKetoglntarate mw fceo Arginine and Praline Catabolism Urea Metabolism Mammals Excretion in urine Microorganisms Urease H20 II S C 2 NHS 002 NH2 Urease Histidine N N o 3 NHA H20 NH H ch L CH 4L ch HJNrCrCOCr Wmquot HCrCOO Urumqi HZCiCOU Ammonia Hymns Lynne Umam 4Imldazolone 5Pmplonate Histidine 900 900 9H2 THF Niamwmw CHZ CH 9N2 2 HNCHNHCCOO HgNicicoo a H um am H My man 4Imidazolone NFormiminaglntamate Glutamate 5 opionate F Formimino Tetrahydrofolate H HZN N N N 10 O H 000 0 fl NNGHL l c NicHrCHzicHz an n Huf Operon of Kebsiela aeragenes FALL 2005 CHEM 153C DISCUSSION NOVEMBER 3 2005 GLUCONEOGENESIS GLYOXYLATE CYCLE AND METABOLIC REGULATION A GLUCONEOGENESIS CYTOSOL AND MITOCHONDRIAL MATRIX Purpose Synthesis of Glucose from noncarbohydrate precursors Glycolysis versus Glucongeogenesis irreversible steps and their counterparts PEP 9 Pyruvate Pyruvate kinase cytosol The Cori Cycle Synthesis of Glucose and ATP from Lactate in skeletal muscle B GLYOXYLATE CYCLE GLYOXYSOME OF PLANTS UNICELLULAR ORGANISMS Purpose Net synthesis of Glucose from AcetylCoA Special enzymes Isocitrate lyase and Malate synthase Anaplerotic reaction Replenishes TCA cycle intermediates C REGULATION OF CARBOHYDRATE METABOLISM The balance ofglycolysis and gluconeogenesis is under hormonal control glucagon vs insulin Metabolic signals of high energy charge ATP NADH G6P AcetylCoA Citrate SuccinylCoA PalmitoylCoA Metabolic signals of low energy charge AMP ADP NAD Generally catabolic enzymes are activated by metabolic signals of low energy charge Likewise anabolic enzymes are activated by metabolic signals of high energy charge Cholesterol Hom eostasis and Hyperlipidemia Dev 72nn5 Chem 1531 Peter A Edmm Depz mems nlBinlngiczl Chem39slly and Mad n2 Hyperlipidemiz 1212mm hlnnd chnlvslernl andnrlrigryceridvsj is inked In am 1 man and d zhelvs gt5n mu demls in LISA msuhlmm zlhernsclernsis and cardinvasculzr disease 1 3922nd n A have cardinvasculzrd gas 21 type 1m helvsgt5 dizh 1 Ih s mhernsclerns39s e mzjnrczuse nldemh 1m quot3 quot quot9 nngmgmnhy mam es A leslnnsand N A ma u 7 1Esnnsltx Wn 39 39 mlusnn are 39 1 1 mlm D1abetes hypevhp1dem1a Wma m Obesity Trends Among us Adults ERFSS199119962004 smu mm m wabmn mm gmm sw Damnquot 1 1 DNaDm Dams Atherosclerosis plaque formtion thrombus and MI Human atherosclerotic rlao e normal human aneiy usaii Miser plaque shoulder site quot3quotquot 5 otrurture athromhus 11m Symmnm39nrmzny is death Atherosclerosis Risk factors include high levels of plasma LDL cholesterol low levels orplasma HDL cholesterol obesit diabetes and metabolic syndrome smokin male or meno ausal female high levels of plasma LPa high blood pressure BP gene ics high homocysteine MlHlDrlS Bf Amerlcans take drugs In lower LDL ralse HDLi lower tr EIF i eat dlabetes all at the rust of billions of oollars Treatments fur ooesityi inoluoing surgeiyi w also very common ano oostlv Plasna Lipoproteins transport insolubldhydrophohlc lipidsi ch lom cro Epitope for LDL receptor t a HDL is mhernrnrnlec lve llevels higher in temalosgtmalesl Viol thioh in metabolic syndrome Cholesterol synthesis and endocytosis via LDL receptors KX39K m Target nlSIzlin drugs 9 nu w 1gtS1SB in mm A A AM K l l r l l 5 7 Av Jve Wm Wm WM Lipnprnleins Irznspn insnluhle n the bland In sues lnr slnrzge zdlpnse lissuel energy ise lmusclel nr slruclure lchnleslemll LnLR Wf W m l aim l mew 391 inncpmm I mm c y ii iii new mm Ill 1 mummy unlnm ywnyr chnlmunl 2 ll mice yceride L munmu 337 muscle and all Fzmy acids and gyceml lhium 39 Hydrolysis of Triglycerides by Lipoprotein Lipase Llrmvmlun IIDse Ishnund In mdmhellll cels lining me mm mees in Bus usere um miscle 39 re Mfr ycerme Tel pnprnlein cnrel Exam 11 Chemistry 153C Fall 2004 Please print and sign your full name below and provide your student ID On the subsequent pages please print your last name The exam should be completed in 50 minutes The only materials allowed on your desk are pencilpen and eraser Calculators are not needed and books and notes are not allowed Printed Name Last First Student ID Signature Points Page 2 22 Page 3 14 Page 4 14 Page 5 16 Page 6 14 Page 7 20 Total l 00 Page 2 of7 Exam II Chem 153C Fall 04 Name 1 The man in the moon possesses A4 A5 A6 and A9 desaturases Using a combination of elongation and desaturation illustrate the following synthesis that occurs in the man in the moon s liver cell Indicate the order of desaturation and elongation and use abbreviations like below for the intermediate forms 6 points C160 9 C223A8A12A15 2 Pyruvate is poised in metabolic pathways to participate in Energy Regenerating and Energy Utilizing pathways according to the Atkinson Energy Charge Hypothesis Provide 4 reactions in which pyruvate can be a substrate or a product including cofactors and enzyme names Structures are not necessary List whether this reaction is Energy Utilizing U Energy Regenerating R or Neither N 16 pointsi4 box A B Page 3 of7 Exam II Chem 153C Fall 04 Name 3 It is possible to formulate a pathway whereby all of the substrates including the reactive forms of coenzymes needed for the biosynthesis of fatty acids as catalyzed by the fatty acyl synthase complex can be derived from citrate in the cytosol 139 e in the cytoplasm outside the mitochondrion Propose a series of reactions starting with citrate which might accomplish this utilizing only enzymes and coenzymes normally present in the cytosol Use structural formulas to indicate substrates and products of the reactions except for coenzymes for which common abbreviations may be employed Note that products derived from citrate may be used as reactants in other reactions if necessary Only the reactions need be shown not the number of times they might participate 12 points 4 What do you want to be when you grow up 2 points Page 4 of7 Exam II Chem 153C Fall 04 Name 5 You are tracing the conversion of aspartate into alphaketoglutarate but there is a mutation in citrate synthase so the TCA cycle can not accommodate this conversion How is aspartate converted to alpha ketoglutarate Provide structures and the names of cofactors Enzyme names are not required 14 points aspa rtaie alpthakemglularale Page 5 of7 Exam II Chem 153C Fall 04 Name 6 You visit a homeopathic doctor because you are not feeling well After doing a complete blood analysis he determines that your levels of homocysteine are high and your quot 39 39 and S ad 39 quot 39 39 levels are low but he does not nd any mutations in the enzymes of the enzymatic cycle for the formation of methionine and Sadenosylmethionine He also notices that the enzymes are all present He suggests that you try taking glycine tablets to correct the defect a What is the potential defect that leads to high homocysteine and low methionine concentrations assuming the enzymes themselves are not defective 3 points b Provide a pathway by which glycine can alleviate this problem 6 points 7 An infant has highlevels of phenylalanine in the blood and phenyllactate and phenylacetate in the urine a What is this disease called and what enzyme is defective 3 points b To develop treatments for this disease you take a liver biopsy and culture the cells in your laboratory You find that when the cells are grown in an anaerobic culture chamber phenylalanine accumulates but when you change the culture chamber to an aerobic environment phenylalanine no longer accumulates but homogentisate now is present as well as acetoacetylCoA and fumarate Briefly how can you explain this result The complete pathway is not required 4 points Page 5 an Exam Chzm 1530 m 4 Name 2 Yanm 15mg m camersmnaflzucmz mm acetaaceme andace yl cm Pm slnlchnes Andthz names afcafacmxs Enzyme names are mm 2an 14mm eu me 5 LL Acecylcmx Aceloacetate Chem 153C 112107 Desaturases and PUFAs Fatty acids in Eukaryotic Cells Melting point 160 palmitic 631 180 stearic 696 161 cis A9 palmitoleic 05 181 cis A9 oleic 134 182 cis A912 linoleic 90 183 cis A91215 linolenic 170 204 cis A581114 arachidonic 495 1821 trans A9 elaidic 430 Oreos with trans fats Serving size is three cookies 160 calories 7 total fat grams 15 grams saturated fat 55 grams of UFO unidentified fatquot including 25 g transfat After the Oreo lawsuit New Oreos without trans fats Serving size is three cookies 160 calories 7 total fat grams 2 grams saturated fat 1 gram polyunsaturated fat 3 grams monounsaturated fat 1 gram unidentified fat The oreo lawsuit led to changes in transfat content in lots of fast foods some were quicker to change than others February 8 2006 Large fries at MacDonald39s contain 30 g fat 8 g transfat December 6 2006 New York bans transfats at City restaurants January 30 2007 MacDonald39s picks new trans fatfree oil Fatty acid desaturases in human cells A9 n7 H A6 n4 cc o ll A5 n3 CH2nCSC0A A4 n2 n number of C from carbonyl and all must be saturated Double bond introduced is always cis Essential fatty acids in seed oils Linoleio acid Linolenio acid by weight by weight safflower 446 sunflower 307 walnut 306 30 soybean 89 12 wheat germ 55 06 flax 49 203


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