PURINE METABOLISM CH O-P CH O-P CH O-P CH O-P NH NH NH NH 2 2 2 2 H C 2 H C H C HC O H O H O NH O NHCOCH NH 2 2 2 2 2 2 CHO CHO CH Formyl- Glutamine Glutamate OC OC C C H H H H H H Glycine H H or NH H folate NH ADP N H OH H H H H 4 ATP Pi HN = NH ADP ATP A MP O-P-O-P H O H ATP ADP+P Gln H O Glu H N 2 PP H folate 2 ATP Pi 2 OH OH OH OH OH OH OH OH Ribose-P 4 Ribose-P Ribose-P Ribose-P 5-P-ribose 5-P-ribosyl- 5-P-Ribosylamine N1-(5-P-ribosyl)glycinamide N2-formyl-N1-(5-P-ribosyl) 2-(formamido)-N1- 5-amino-1-(P-ribosyl)- 2.7.6.1 pyrophosphate 2.4.2.14 6.3.4.13 2.1.2.2 6.3.5.3 (5-P-ribosyl)acetamidine 6.3.3.1 ADP GDP AMP GTP glycinamide - imidazole (PRPP) GDP ADP ATP ATPGMP -OOCCHCH COO- -OOCCHCH COO- 2 2 O O O CO NH - - - - 2 OOCCHCH COO C HN CO OOCCHCH2COO - C NH 2 C N C NH NH NH OOC 4.1.1.21 N 2 HN H N + NH N C C H2N C 2 C C Aspartate NH3 C CH GDP CH CH Formyl- CH CH Aspartate CH ADP HC C HC C OHC C H4folate C C Pi N Pi N H O N N N ADP C N GTP N 2 N H4folate H N H N N 2 Fumarate 2 Pi ATP H N Ribose-P Ribose-P H Ribose-P Ribose-P Ribose-P 2 E 4.3.2.2 Ribose-P YCL C Adenylosuccinate 4.3.2.2 E Inosine- 5-formamido-1-(5-P-ribosyl)- 5-amino-1-(5-P-ribosyl)- 5-amino-1-(5-P-ribosyl-) 5-amino-1-(5-P-ribosyl) ID P 3.5.4.10 2.1.2.3 T i m i d a z ole-4-(N)-[1,2-dicarboxy-6.3.2.6 O imidazole-4-carboxamide imidazole-4-carboxylate E IMP imidazole-4-carboxamide L ethyl]-carboxamide C U N C E I RNA N S E I 2.7.7.6 2.7.7.6 R D L TCA I Fumarate U C C CYCLE P U RNA A RNA RNA n N n n+1 RNAn+1 DNA S NH2 E 2.7.7.7 2.7.7.7 E NH C T 2 N O D A C I N N C H T N C CH C P DNA N O DNA DNA DNA n HN S CH HC n n+1 n+1 C E C N L O HC C N CH O C H N N C C P U (P-O-)P-O-P-OCH C I 2 H2N N N N ATP Deoxy-ATP PP N DeoxyGTP R (P-O-)P-O-P-OCH2 O i H HN C GTP T O 2.4.2.8 CH + NADP H H PRPP + + C C S NADP NADPH+H H H NADPH+H H H 2N N E H N E H H NDP NAD+ O H T D NDP OH H I A 1.6.4.5 H O C ADP 1.6.4.5 ADP T OH 2.7.4.6 2 (P-O-)P-O-P-OCH2 H OH N O 2.7.4.6 P NTP HN C 2.7.4.6 2.7.4.6 O E S L NTP + CH Thioredoxin O (S-S) NADH+H Thioredoxin ATP -SH C C ATP H T C (2SH) (S-S) H H U n H2N N H H P h i I i N N o x redo 1.17.4.1 D Deoxy-ADP O Ribose-P-O-P OH H ADP 1.17.4.1 GDP DeoxyGDP NH C S 2 N Glutamine Glutamate O E C HN C ADP N ADP C D N I N C CH H O PPi C T N 2.7.4.3 CH C C 2 2.7.4.8 H O N CH HC + O N AMP E C ATP N H O NH4 ATP C L ATP C N 2 H Ribose-P N N C C H2 N U Ribose-P H O Ribose-P N 2 GMP AMP 3.5.4.6 O XMP 6.3.4.1 3.1.3.31 E O ENZYMES NH O S 2 C G C C 2.7.7.7 DNA-directed DNA polymerase E C N P N 1.1.1.205 IMPdehydrogenase N H O i A N H O H2O D 2 H N C 2 C 3.1.3.5 5'-Nucleotidase V HN Xanthine oxidase I N C HN C 1.1.3.22 L S 3.1.3.31 CH CH 3.1.3.31 CH 3.1.3.31 1.6.4.5 Thioredoxin reductase 3.1.3.31 Nucleotidase E CH A O + H C C H H O C 1.6.6.8 GMP reductase 3.2.2.1 Purine nucleosidase NH S C C + 2 C E G HC H O 4 P C Pi 2 N N Pi O NH4 H N N i S 1.7.3.3 Urate oxidase 3.2.2.2 Inosine nucleosidase L N N O A 2 N N N H2 C 1.17.4.1 3.2.2.4 AMP nucleosidase V Ribose Ribose Ribose Ribose A Ribonucleoside diphosphate L U L 2.1.2.2 P-ribosylglycinamide 3.2.2.7 Adenosine nucleosidase A N ADENOSINE INOSINE XANTHOSINE GUANOSINE 3.5.1.5 Urease S 3.5.4.4 V NH Pi O 3.5.4.15 formyl-transferase reductase 3.5.3.4 Allantoicase C 2 Pi O A N Pi 2.4.2.1 C N Pi 2.1.2.3 P-ribosylaminoimidazole 3.5.4.2 Adenine deaminase N C O C G 3.5.4.3 Guanine deaminase E PPi Ribose-1-P 2.4.2.1 HN C N carboxamide formyl S 2.4.2.1 HN C 2.4.2.1 E N CH C C transferase 3.5.4.4 Adenosine deaminase I CH E N Ribose-1-P CH R HC C H 3.5.4.6 AMP deaminase S N C Purine nucleoside phosphorylase N Ribose-1-P + C C Ribose-1-P 2.4.2.1 U A H NH H O N N H2O 4 CH H2O O 2 2 O N C C 2.4.2.7 Adenine P-ribosyl transferase 3.5.4.10 IMP cyclohydrolase P B PRPP 2 H2N N HC C H N 2.4.2.8 Hypoxanthine P-ribosyl 3.5.4.15 Guanosine deaminase N H H N 3.5.4.3 transferase 4.1.1.21 P-ribosylaminoimidazole ADENINE H HYPOXANTHINE XANTHINE GUANINE 2.4.2.14 Amidophosphoribosyl transferase 4.3.2.2 Adenylosuccinate lyase 3.5.4.2 1.1.3.22 + 2.7.1.17 Ribokinase carboxylase OH OH O NH4 2.7.4.3 Adenylate kinase 6.3.2.6 P-ribosylaminoimidazolesuccino- O O H H2O NH2 O NH C 2.7.4.4 Nucleoside-phosphate kinase carboxamide synthase C N H N C H N C N 2.7.4.6 Nucleoside-diphosphate kinase 6.3.3.1 P-ribosylformylglycinamidine- H N H2 2 2 HN C 2 H O CO CO 2.7.4.8 Guanylate kinase cyclo-ligase N 2CO 2 CO 2 2H O CHO CO C C C C 2.7.4.11 (Deoxy)adenylate kinase 6.3.4.1 GMP synthase O 2 C N H O O I O 2 2 C 2 E H C N H H2O O H NH 2H O H 2.7.6.1 Ribose phosphate pyro- 6.3.4.13 P-ribosylamine-glycine ligase T O NH N 2 O N N 2 N H CO O N H O I H 2 phosphate kinase 6.3.5.3 P-ribosylformylglycinamidine E 2 H 2 2 R H R + Glyoxylate 1.1.3.22 2.7.7.6 DNA-directed RNA polymerase synthase U C 4NH4 3.5.3.4 A llantoic acid 3.5.3.4 Allantoin 1.7.3.3 URIC ACID P Urea X 3.5.1.5. Urea E Ammonia H2O2 Marine Sharks, Teleost (bony) fish O t h e r Mammals P r im a t e s , b irds invertebrates amphibia reptiles insects Designed by Donald Nicholson c 2002 IUBMB.