Thiol dioxygenases: Unique families of cupin proteins

Amino Acids

Volumn 41, Issue 1, 2011, Pages 91-102

  Stipanuk, Martha H ^a   Simmons, Chad R ^a,d   Karplus, P Andrew ^b   Dominy, John E ^a,c  

^a Department of Obstetrics Gynecology   (United States)

^b OREGON STATE UNIVERSITY   (United States)

^c HARVARD MEDICAL SCHOOL   (United States)

^d ARIZONA STATE UNIVERSITY   (United States)

Author keywords

Cupin proteins; Cysteamine dioxygenase; Cysteine dioxygenase; Domain of unknown function 1637 (DUF1637); Iron dependent enzymes; Thiols

Indexed keywords

CARBOXYLIC ACID; CUPIN; CYSTEAMINE DIOXYGENASE; CYSTEINE DIOXYGENASE; DIOXYGENASE; MEMBRANE PROTEIN; THIOL DIOXYGENASE DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; BACILLUS CEREUS; BACILLUS SUBTILIS; BIOGENESIS; CRYSTAL STRUCTURE; ENZYME ACTIVE SITE; ENZYME METABOLISM; ENZYME SPECIFICITY; ENZYME STRUCTURE; ISOMERIZATION; NONHUMAN; NUCLEOTIDE SEQUENCE; OXIDATION; PRIORITY JOURNAL; PROKARYOTE; PROTEIN ANALYSIS; PROTEIN CROSS LINKING; PROTEIN FOLDING; PROTEIN INTERACTION; PROTEIN MOTIF; PROTEIN STRUCTURE; REVIEW; SEQUENCE ALIGNMENT; SEQUENCE HOMOLOGY; SULFOXIDATION;

ANIMALS; BIOCATALYSIS; CYSTEINE DIOXYGENASE; DIOXYGENASES; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN CONFORMATION;

BACTERIA (MICROORGANISMS); EUKARYOTA; MAMMALIA; PROKARYOTA;

EID: 79960409992     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-010-0518-2     Document Type: Review

References (44)

1. Aluri S, de Visser SP (2007) The mechanism of cysteine oxygenation by cysteine dioxygenase enzymes. J Am Chem Soc 129:14846-14847 (Pubitemid 350230695)
2. Anand R, Dorrestein PC, Kinsland C, Begley TP, Ealick SE (2002) Structure of oxalate decarboxylase from Bacillus subtilis at 1.75 A resolution. Biochemistry 41:7659-7669 (Pubitemid 34627793)
3. Bruland N, Wübbeler JH, Steinbüchel A (2009) 3-mercaptopropio-nate dioxygenase, a cysteine dioxygenase homologue, catalyzes the initial step of 3-mercaptopropionate catabolism in the 3, 3-thiodipropionic acid-degrading bacterium Variovorax paradox-us. J Biol Chem 284:660-672
4. Cavallini D, Scandurra R, Demarco C (1963) The enzymatic oxidation of cysteamine to hypotaurine in the presence of sulfide. J Biol Chem 238:2999-3005
5. Cavallini D, Federici G, Ricci G, Dupre S, Antonucci A (1975) The specificity of cysteamine oxygenase. FEBS Lett 56:348-351
6. Chen CJ, Lin YH, Huang YC, Liu MY (2006) Crystal structure of rubredoxin from Desulfovibrio gigas to ultra-high 0.68 A resolution. Biochem Biophys Res Commun 349:79-90
7. Dominy JE Jr, Simmons CR, Karplus PA, Gehring AM, Stipanuk MH (2006) Identification and characterization of bacterial cysteine dioxygenases: a new route of cysteine degradation for eubacte-ria. J Bacteriol 188:5561-5569 (Pubitemid 44157313)
8. Dominy JE Jr, Simmons CR, Hirschberger LL, Hwang J, Coloso RM, Stipanuk MH (2007) Discovery and characterization of a second mammalian thiol dioxygenase, cysteamine dioxygenase. J Biol Chem 282:25189-25198 (Pubitemid 47372806)
9. Dominy JE Jr, Hwang J, Guo S, Hirschberger LL, Zhang S, Stipanuk MH (2008) Synthesis of amino acid cofactor in cysteine dioxygenase is regulated by substrate and represents a novel post-translational regulation of activity. J Biol Chem 283:12188-12201
10. Dunwell JM, Khuri S, Gane PJ (2000) Microbial relatives of the seed storage proteins of higher plants: conservation of structure and diversification of function during evolution of the cupin super-family. Microbiol Mol Biol Rev 64:153-179 (Pubitemid 30143844)
11. Dunwell JM, Culham A, Carter CE, Sosa-Aguirre CR, Goodenough PW (2001) Evolution of functional diversity in the cupin superfamily. Trends Biochem Sci 26:740-746 (Pubitemid 34014841)
12. Fusetti F, Schroter KH, Steiner RA, van Noort PI, Pijning T, Rozeboom HJ, Kalk KH, Egmond MR, Dijkstra BW (2002) Crystal structure of the copper-containing quercetin 2, 3-dioxy-genase from Aspergillus japonicus. Structure (Camb) 10:259-268 (Pubitemid 34164603)
13. Hirschberger LL, Daval S, Stover PJ, Stipanuk MH (2001) Murine cysteine dioxygenase gene: structural organization, tissue-specific expression and promoter identification. Gene 277:153-161 (Pubitemid 32972117)
14. Hosokawa Y, Matsumoto A, Oka J, Itakura H, Yamaguchi K (1990) Isolation and characterization of a cDNA for rat liver cysteine dioxygenase. Biochem Biophys Res Commun 168:473-478 (Pubitemid 20164566)
15. Ito N, Phillips SE, Stevens C, Ogel ZB, McPherson MJ, Keen JN, Yadav KD, Knowles PF (1991) Novel thioether bond revealed by a 1.7 A crystal structure of galactose oxidase. Nature 350:87-90 (Pubitemid 21926129)
16. Jaroszewski L, Schwarzenbacher R, von Delft F, McMullan D, Brinen LS, Canaves JM, Dai X, Deacon AM, DiDonato M, Elsliger MA, Eshagi S, Floyd R, Godzik A, Grittini C, Grzechnik SK, Hampton E, Levin I, Karlak C, Klock HE, Koesema E, Kovarik JS, Kreusch A, Kuhn P, Lesley SA, McPhillips TM, Miller MD, Morse, Moy K, Ouyang J, Page R, Quijano K, Reyes R, Rezezadeh F, Robb A, Sims E, Spraggon G, Stevens RC, van den Bedem H, Velasquez J, Vincent J, Wang X, West B, Wolf G, Xu Q, Hodgson KO, Wooley J, Wilson IA (2004) Crystal structure of a novel manganese-containing cupin (TM1459) from Thermotoga maritima at 1.65 A resolution. Proteins 56:611-614 (Pubitemid 38924973)
17. Kleffmann T, Jongkees SA, Fairweather G, Wilbanks SM, Jameson GNJ (2009) Mass-spectrometric characterization of two post-translational modifications of cysteine dioxygenase. Biol Inorg Chem 14:913-921
18. Ko TP, Day J, McPherson A (2000) The refined structure of canavalin from jack bean in two crystal forms at 2.1 and 2.0 A resolution. Acta Crystallogr D Biol Crystallogr 56(Pt 4):411-420 (Pubitemid 30231221)
19. Lawrence MC, Izard T, Beuchat M, Blagrove RJ, Colman PM (1994) Structure of phaseolin at 2.2 A resolution. Implications for a common vicilin/legumin structure and the genetic engineering of seed storage proteins. J Mol Biol 238:748-776
20. McCann KP, Akbari MT, Williams AC, Ramsden DB (1994) Human cysteine dioxygenase type I: primary structure derived from base sequencing of cDNA. Biochim Biophys Acta 1209:107-110 (Pubitemid 24351996)
21. McCoy JG, Bailey LJ, Bitto E, Bingman CA, Aceti DJ, Fox BG, Phillips GN Jr (2006) Structure and mechanism of mouse cysteine dioxygenase. Proc Natl Acad Sci USA 103:3084-3089 (Pubitemid 43346428)
22. Pierce BS, Gardner JD, Bailey LJ, Brunold TC, Fox BG (2007) Characterization of the nitrosyl adduct of substrate-bound mouse cysteine dioxygenase by electron paramagnetic resonance: electronic structure of the active site and mechanistic iimplica-tions. Biochemistry 46:8569-8578 (Pubitemid 47106108)
23. Richerson RB, Ziegler DM (1987) Cysteamine dioxygenase. Methods Enzymol 143:410-415
24. Rogers MS, Baron AJ, McPherson MJ, Knowles PF, Dooley DM (2000) Galactose oxidase pro-sequence cleavage and cofactor assembly are self-processing reactions. J Am Chem Soc 122:990-991 (Pubitemid 30094425)
25. Rogers MS, Hurtado-Guerrero R, Firbank SJ, Halcrow MA, Dooley DM, Phillips SE, Knowles PF, McPherson MJ (2008) Cross-link formation of the cysteine 228-tyrosine 272 catalytic cofactor of galactose oxidase does not require dioxygen. Biochemistry 47:10428-10439
26. Rossmann MG, Abad-Zapatero C, Murthy MR, Liljas L, Jones TA, Strandberg B (1983) Structural comparisons of some small spherical plant viruses. J Mol Biol 165:711-736
27. Sakakibara S, Yamaguchi K, Hosokawa Y, Kohashi N, Ueda I (1976) Purification and some properties of rat liver cysteine oxidase (cysteine dioxygenase). Biochim Biophys Acta 422:273-279
28. Schnell R, Sandalova T, Hellman U, Lindqvist Y, Schneider G (2005) Siroheme- and [Fe4-S4]-dependent NirA from Mycobacterium tuberculosis is a sulfite reductase with a covalent Cys-Tyr bond in the active site. J Biol Chem 280:27319-27328 (Pubitemid 41040773)
29. Simmons CR, Hirschberger LL, Machi MS, Stipanuk MH (2006a) Expression, purification, and kinetic characterization of recom-binant rat cysteine dioxygenase, a non-heme metalloenzyme necessary for regulation of cellular cysteine levels. Protein Expr Purif 47:74-81
30. Simmons CR, Liu Q, Huang Q, Hao Q, Begley TP, Karplus PA, Stipanuk MH (2006b) Crystal structure of mammalian cysteine dioxygenase. A novel mononuclear iron center for cysteine thiol oxidation. J Biol Chem 281:18723-18733 (Pubitemid 44035533)
31. 2+-bound persulfenate intermediate in cysteine dioxyenase. Biochemistry 47:11390-11392
32. Stipanuk MH (1986) Metabolism of sulfur-containing amino acids. Annu Rev Nutr 6:179-209
33. Stipanuk MH (2004) Sulfur amino acid metabolism: pathways for production and removal of homocysteine and cysteine. Annu Rev Nutr 24:539-577 (Pubitemid 38938803)
34. Stipanuk MH, Londono M, Lee JI, Hu M, Yu AF (2002) Enzymes and metabolites of cysteine metabolism in nonhepatic tissues of rats show little response to changes in dietary protein or sulfur amino acid levels. J Nutr 132:3369-3378 (Pubitemid 35304246)
35. Stipanuk MH, Londono M, Hirschberger LL, Hickey C, Thiel DJ, Wang L (2004) Evidence for expression of a single distinct form of mammalian cysteine dioxygenase. Amino Acids 26:99-106 (Pubitemid 38270763)
36. Stipanuk MH, Ueki I, Dominy JE Jr, Simmons CR, Hirschberger LL (2009) Cysteine dioxygenase: a robust system for regulation of cellular cysteine levels. Amino Acids 37:55-63
37. Tanner A, Bowater L, Fairhurst SA, Bornemann S (2001) Oxalate decarboxylase requires manganese and dioxygen for activity. Overexpression and characterization of Bacillus subtilis YvrK and YoaN. J Biol Chem 276:43627-43634
38. Whittaker MM, Whittaker JW (2003) Cu(I)-dependent biogenesis of the galactose oxidase redox cofactor. J Biol Chem 278:22090-22101 (Pubitemid 36792619)
39. Whittaker MM, Kersten PJ, Nakamura N, Sanders-Loehr J, Schweizer ES, Whittaker JW (1996) Glyoxal oxidase from Phanerochaete chrysosporium is a new radical-copper oxidase. J Biol Chem 271:681-687
40. Whittaker MM, Kersten PJ, Cullen D, Whittaker JW (1999) Identification of catalytic residues in glyoxal oxidase by targeted mutagenesis. J Biol Chem 274:36226-36232
41. Woo EJ, Dunwell JM, Goodenough PW, Marvier AC, Pickersgill RW (2000) Germin is a manganese containing homohexamer with oxalate oxidase and superoxide dismutase activities. Nat Struct Biol 7:1036-1040
42. Yamaguchi K, Hosokawa Y, Kohashi N, Kori Y, Sakakibara S, Ueda I (1978) Rat liver cysteine dioxygenase (cysteine oxidase). Further purification, characterization, and analysis of the activation and inactivation. J Biochem (Tokyo) 83:479-491 (Pubitemid 8282048)
43. Ye S, Wu X, Wei L, Tang D, Sun P, Bartlam M, Rao Z (2007) An insight into the mechanism of human cysteine dioxygenase. Key roles of the thioether-bonded tyrosine-cysteine cofactor. J Biol Chem 282:3391-3402 (Pubitemid 47084325)
44. Zhang Y, Colabroy KL, Begley TP, Ealick SE (2005) Structural studies on 3-hydroxyanthranilate-3, 4-dioxygenase: the catalytic mechanism of a complex oxidation involved in NAD biosynthesis. Biochemistry 44:7632-7643 (Pubitemid 40740747)