Structural characterization of the mitomycin 7-O-methyltransferase

Proteins: Structure, Function and Bioinformatics

Volumn 79, Issue 7, 2011, Pages 2181-2188

  Singh, Shanteri ^a   Chang, Aram ^a   Goff, Randal D ^a   Bingman, Craig A ^a   Grüschow, Sabine ^b   Sherman, David H ^b   Phillips Jr , George N ^a   Thorson, Jon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b UNIVERSITY OF MICHIGAN   (United States)

Author keywords

Biosynthesis; Cancer; Methyltransferase; Mitomycin; Natural product; S adenosyl L methionine; X ray crystallography

Indexed keywords

METHYLTRANSFERASE; MITOMYCIN 7 O METHYLTRANSFERASE; MITOMYCIN A; MITOMYCIN B; MITOMYCIN C; S ADENOSYLHOMOCYSTEINE; S ADENOSYLMETHIONINE; UNCLASSIFIED DRUG;

ACID BASE BALANCE; ALKYLATION; ARTICLE; BINDING SITE; COMPLEX FORMATION; CRYSTAL STRUCTURE; ENZYME ACTIVE SITE; ENZYME STRUCTURE; ENZYME SUBSTRATE COMPLEX; OXIDATION REDUCTION POTENTIAL; PRIORITY JOURNAL; STRUCTURAL HOMOLOGY;

AMINO ACID SEQUENCE; BACTERIAL PROTEINS; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; METHYLTRANSFERASES; MITOMYCIN; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PROTEIN BINDING; PROTEIN FOLDING; PROTEIN STRUCTURE, TERTIARY; RECOMBINANT PROTEINS; S-ADENOSYLHOMOCYSTEINE; SEQUENCE ALIGNMENT; STREPTOMYCES; STRUCTURAL HOMOLOGY, PROTEIN;

STREPTOMYCES LAVENDULAE;

EID: 79958767718     PISSN: 08873585     EISSN: 10970134     Source Type: Journal    
DOI: 10.1002/prot.23040     Document Type: Article

References (42)

1. Hata T, Sugawara R. Mitomycin, a new antibiotic from Streptomyces. II. Description of the strain. J Antibiot 1956; 9: 147-151.
2. Hata T, Hoshi T, Kanamori K, Matsumae A, Sano Y, Shima T, Sugawara R. Mitomycin, a new antibiotic from Streptomyces. I. JAntibiot Ser A 1956; 9: 141-146.
3. Wakaki S, Marumo H, Tomioka K, Shimizu G, Kato E, Kamada H, Kudo S, Fujimoto Y. Isolation of new fractions of antitumor mitomycins. Antibiot Chemother 1958; 8: 228-240.
4. Begleiter A. Clinical applications of quinone-containing alkylating agents. Front Biosci 2000; 5: E153-E171.
5. Galm U, Hager MH, van Lanen SG, Ju J, Thorson JS, Shen B. Antitumor antibiotics: bleomycin, enediynes, and mitomycin. Chem Rev 2005; 105: 739-758.
6. McKeown SR, Coweny RL, Williams KJ. Bioreductive drugs: from concept to clinic. Clin Oncol (R Coll Radiol) 2007; 19: 427-442.
7. Rockwell S, Dobrucki IT, Kim EY, Marrison ST, Vu VT. Hypoxia and radiation therapy: past history, ongoing research, and future promise. Curr Mol Med 2009; 9: 442-458.
8. Bezanson GS, Vining LC. Studies on the biosynthesis of mitomycin C by Streptomyces verticillatus. Can J Biochem 1971; 49: 911-918.
9. Anderson MG, Kibby JJ, Rickards RW, Rothschild JM. Biosynthesis of the mitomycin antibiotics from 3-amino-5-hydroxybenzoic acid. J Chem Soc Chem Commun 1980; 1980: 1277-1278.
10. 15N) citrulline in mitomycin biosynthesis by Streptomyces verticillatus. J Antibiot (Tokyo) 1975; 10: 841-843.
11. Hornemann Y, Kehrer JP, Nunez CS, Ranieri RL. D-glucosamine and L-citrulline, precursors in mitomycin biosynthesis by Streptomyces verticillatus. J Am Chem Soc 1974; 96: 320-322.
12. Mao Y, Varoglu M, Sherman DH. Molecular characterization and analysis of the biosynthetic gene cluster for the antitumor antibiotic mitomycin C from Streptomyces lavendulae NRRL 2564. Chem Biol 1999; 6: 251-263.
13. Sitachitta N, Lopanik NB, Mao Y, Sherman DH. Analysis of a parallel branch in the mitomycin biosynthetic pathway involving the mitN-encoded aziridine N-methyltransferase. J Biol Chem 2007; 282: 20941-20947.
14. Gruschow S, Chang LC, Mao Y, Sherman DH. Hydroxyquinone O-methylation in mitomycin biosynthesis. J Am Chem Soc 2007; 129: 6470-6476.
15. Zhang C, Weller RL, Thorson JS, Rajski SR. Natural product diversification using a non-natural cofactor analogue of S-adenosyl-L-methionine. J Am Chem Soc 2006; 128: 2760-2761.
16. Zhang C, Albermann C, Fu X, Peters NR, Chisholm JD, Zhang G, Gilbert EJ, Wang PG, Van Vranken DL, Thorson JS. RebG- and RebM-catalyzed indolocarbazole diversification. Chembiochem 2006; 7: 795-804.
17. Singh S, McCoy JG, Zhang C, Bingman CA, Phillips GN, Jr, Thorson JS. Structure and mechanism of the rebeccamycin sugar 4'-O-methyltransferase RebM. J Biol Chem 2008; 283: 22628-22636.
18. Lukinavicius G. Lapiene V, Stasevskij Z, Dalhoff C, Weinhold E, Klimasauskas S. Targeted labeling of DNA by methyltransferase-directed transfer of activated groups (mTAG). J Am Chem Soc 2007; 129: 2758-2759.
19. Klimasauskas S, Weinhold E. A new tool for biotechnology: AdoMet-dependent methyltransferases. Trends Biotechnol 2007; 25: 99-104.
20. Peters W, Willnow S, Duisken M, Kleine H, Macherey T, Duncan KE, Litchfield DW, Lüscher B, Weinhold E. Enzymatic site-specific functionalization of protein methyltransferase substrates with alkynes for click labeling. Angew Chem Int Ed Engl 2010; 49: 5170-5173.
21. Dalhoff C, Lukinavicius G, Klimasauskas S, Weinhold E. Synthesis of S-adenosyl-L-methionine analogs and their use for sequence-specific transalkylation of DNA by methyltransferases. Nat Protoc 2006; 1: 1879-1886.
22. Dalhoff C, Lukinavicius G, Klimasauskas S, Weinhold E. Direct transfer of extended groups from synthetic cofactors by DNA methyltransferases. Nat Chem Biol 2006; 2: 31-32.
23. Sreenath HK, Bingman CA, Buchan BW, Seder KD, Burns BT, Geetha HV, Jeon WB, Vojtik FC, Aceti DJ, Frederick RO, Phillips GN, Jr, Fox BG. Protocols for production of selenomethionine-labeled proteins in 2-L polyethylene terephthalate bottles using auto-induction medium. Protein Expr Purif 2005; 40: 256-267.
24. Otwinowski Z, Minor W. Processing of X-ray diffraction data collected in oscillation mode. Methods Enzymol 1997; 276: 307-326.
25. Grosse-Kunstleve RW, Adams PD. Substructure search procedures for macromolecular structures. Acta Crystallogr Sect D 2003; 59: 1966-1973.
26. Schneider TR, Sheldrick GM. Substructure solution with SHELXD. Acta Crystallogr Sect D 2002; 58: 1772-1779.
27. Dall'Antonia F, Baker PJ, Schneider TR. Optimization of selenium substructures as obtained from SHELXD. Acta Crystallogr Sect D 2003; 59: 1987-1994.
28. de la Fortelle E, Bricogne G. Maximum-likelihood heavy-atom parameter refinement for multiple insomorphous replacement and multiwavelength anomalous diffraction methods. Methods Enzymol 1997; 276: 472-494.
29. Perrakis A, Morris R, Lamzin VS. Automated protein model building combined with iterative structure refinement. Nat Struct Biol 1999; 6: 458-463.
30. Vagin A, Teplyakov A. MOLREP: an automated program for molecular replacement. J Appl Crystallogr 1997; 30: 1022-1025.
31. Emsley P, Cowtan K. Coot: model-building tools for molecular graphics. Acta Crystallogr Sect D 2004; 60: 2126-2132.
32. Murshudov GN, Vagin AA, Dodson EJ. Refinement of macromolecular structures by the maximum-likelihood method. Acta Crystallogr Sect D 1997; 53: 240-255.
33. Adams PD, Grosse-Kunstleve RW, Hung LW, Ioerger TR, McCoy AJ, Moriarty NW, Read RJ, Sacchettini JC, Sauter NK, Terwilliger TC. PHENIX: building new software for automated crystallographic structure determination. Acta Crystallogr Sect D 2002; 58: 1948-1954.
34. Davis IW, Leaver-Fay A, Chen VB, Block JN, Kapral GJ, Wang X, Murray LW, Arendall WB, III, Snoeyink J, Richardson JS, Richardson DC. MolProbity: all-atom contacts and structure validation for proteins and nucleic acids. Nucleic Acids Res 2007; 35: W375-W383.
35. Laskowski RA, Rullmannn JA, MacArthur MW, Kaptein R, Thornton JM. AQUA and PROCHECK-NMR: programs for checking the quality of protein structures solved by NMR. J Biomol NMR 1996; 8: 477-486.
36. Potterton E, Briggs P, Turkenburg M, Dodson EA. Graphical user interface to the CCP4 program suite. Acta Crystallogr D Biol Crystallogr 2003; 59: 1131-1137.
37. Jansson A, Koskiniemi H, Mantsala P, Niemi J, Schneider G. Crystal structure of a ternary complex of DnrK, a methyltransferase in daunorubicin biosynthesis, with bound products. J Biol Chem 2004; 279: 41149-41156.
38. Cooke HA, Guenther EL, Luo Y, Shen B, Bruner SD. Molecular basis of substrate promiscuity for the SAM-dependent O-methyltransferase NcsB1, involved in the biosynthesis of the enediyne antitumor antibiotic neocarzinostatin. Biochemistry 2009; 48: 9590-9598.
39. Zubieta C, He XZ, Dixon RA, Noel JP. Structures of two natural product methyltransferases reveal the basis for substrate specificity in plant O-methyltransferases. Nat Struct Mol Biol 2001; 8: 271-279.
40. Chang A, Singh S, Bingman CA, Thorson JS, Phillips GN, Jr. Structural characterization of CalO1: A putative orsellinic acid methyltransferase in the calicheamicin biosynthetic pathway. Acta Cryst D 2011; D67: 197-203.
41. Palma PN, Rodrigues ML, Archer M, Bonifácio MJ, Loureiro AI, Learmonth DA, Carrondo MA, Soares-da-Silva P. Comparative study of ortho- and meta-nitrated inhibitors of catechol-O-methyltransferase: interactions with the active site and regioselectivity of O-methylation. Mol Pharmacol 2006; 70: 143-153.
42. Jansson A, Niemi J, Lindqvist Y, Mantsala P, Schneider G. Crystal structure of aclacinomycin-10-hydroxylase, a S-adenosyl-L-methionine-dependent methyltransferase homolog involved in anthracycline biosynthesis in Streptomyces purpurascens. J Mol Biol 2003; 334: 269-280.