In vitro characterization of enzymes involved in the synthesis of nonproteinogenic residue (2S,3S)-β-methylphenylalanine in glycopeptide antibiotic mannopeptimycin

ChemBioChem

Volumn 10, Issue 15, 2009, Pages 2480-2487

  Huang, Yu Ting ^a   Lyu, Syue Yi ^a   Chuang, Pei Hsuan ^a   Hsu, Ning Shian ^a   Li, Yi Shan ^a   Chan, Hsiu Chien ^a   Huang, Chuen Jiuan ^a   Liu, Yu Chen ^a   Wu, Chang Jer ^b   Yang, Wen Bin ^a   Li, Tsung Lin ^a  

^a GENOMICS RESEARCH CENTER   (Taiwan)

^b NATIONAL TAIWAN OCEAN UNIVERSITY   (Taiwan)

Author keywords

Amino acids; Diastereoselectivity; Mannopeptimycin; Methyltransferases; Nonribosomal peptide synthetases

Indexed keywords

AMINO ACID; AMINOTRANSFERASE; BETA METHYLPHENYLALANINE; MANNOPEPTIMYCIN; METHYLTRANSFERASE; PHENYLPYRUVIC ACID; POLYPEPTIDE ANTIBIOTIC AGENT; PROTEIN MPPJ; PROTEIN TYRB; S ADENOSYLMETHIONINE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; DRUG STRUCTURE; ENZYME ANALYSIS; ENZYME ASSAY; ENZYME KINETICS; ENZYME SPECIFICITY; GRAM POSITIVE BACTERIUM; IN VITRO STUDY; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; METHYLATION; MOLECULAR CLONING; NONHUMAN; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

AMINATION; AMINOBUTYRIC ACIDS; ANTI-BACTERIAL AGENTS; ESCHERICHIA COLI; GLYCOPEPTIDES; KINETICS; METHYLTRANSFERASES; RECOMBINANT PROTEINS; STEREOISOMERISM; SUBSTRATE SPECIFICITY; TRANSAMINASES;

METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; POSIBACTERIA;

EID: 70350553834     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200900351     Document Type: Article

References (35)

1. J. A. Ma, Angew. Chem. 2003, 115, 4426;
2. Angew. Chem. Int. Ed. 2003, 42, 4290.
3. G. Cardillo, L. Gentilucci, A. Tolomelli, Mini Rev. Med. Chem. 2006, 6, 293.
4. N. Sitaram, Curr. Med. Chem. 2006, 13, 679.
5. M. S. Butler, A. D. Buss, Biochem. Pharmacol. 2006, 71, 919.
6. C. S. V. Houge-Frydrych, M. L. Gilpin, P. W. Skett, J. W. Tyler, J. Antibiot. 2000, 53, 364.
7. H. He, R. T. Williamson, B. Shen, E. I. Graziani, H. Y. Yang, S. M. Sakya, P. J. Petersen, G. T. Carter, J. Am. Chem. Soc. 2002, 124, 9729.
8. A. Ruzin, G. Singh, A. Severin, Y. Yang, R. G. Dushin, A. G. Sutherland, A. Minnick, M. Greenstein, M. K. May, D. M. Shlaes, P. A. Bradford, Antimicrob. Agents Chemother. 2004, 48, 728.
9. R. G. Dushin, T. Z. Wang, P. E. Sum, H. He, A. G. Sutherland, J. S. Ashcroft, E. I. Graziani, F. E. Koehn, P. A. Bradford, P. J. Petersen, K. L. Wheless, D. How, N. Torres, E. B. Lenoy, W. J. Weiss, S. A. Lang, S. J. Projan, D. M. Shlaes, T. S. Mansour, J. Med. Chem. 2004, 47, 3487.
10. F. E. Koehn, G. T. Carter, Nat. Rev. Drug. Discovery 2005, 4, 206.
11. E. Breukink, B. de Kruijff, Nat. Rev. Drug. Discovery 2006, 5, 321.
12. N. A. Magarvey, B. Haltli, M. He, M. Greenstein, J. A. Hucul, Antimicrob. Agents Chemother. 2006, 50, 2167.
13. C. Milne, A. Powell, J. Jim, M. Al Nakeeb, C. P. Smith, J. Micklefield, J. Am. Chem. Soc. 2006, 128, 11250.
14. U. Hornemann, L. H. Hurley, M. K. Speedie, H. G. Floss, J. Am. Chem. Soc. 1971, 93, 3028.
15. L. J. Mascaro, R. Horhammer, S. Eisenstein, L. K. Seller, K. Mascaro, H. G. Floss, J. Am. Chem. Soc. 1977, 99, 273.
16. X. Yin, T. M. Zabriskie, Microbiology 2006, 152, 2969.
17. J. Yang, J. Pittard, J. Bacteriol. 1987, 169, 4710.
18. R. Finking, M. A. Marahiel, Annu. Rev. Microbiol. 2004, 58, 453.
19. M. B. Smith, J. March, Delocalized Chemical Bonding in March's Advanced Organic Chemistry, John Wiley & Sons, New Jersey, USA, 2007.
20. V. Cerovský, E. Welker, H. A. Scheraga, J. Pept. Res. 2003, 61, 140.
21. J. Yin, A. J. Lin, D. E. Golan, C. T. Walsh, Nat. Protoc. 2006, 1, 280.
22. M. L. Bianconi, J. Biol. Chem. 2003, 278, 18709.
23. M. Pacholec, J. Tao, C. T. Walsh, Biochemistry 2005, 44, 14969.
24. L. M. Nogle, C. W. Mann, W. L. J. Watts, Y. Zhang, J. Pharm. Biomed. Anal. 2006, 40, 901.
25. G. J. Poelarends, R. Saunier, D. B. Janssen, J. Bacteriol. 2001, 183, 4269.
26. G. J. Poelarends, W. H. J. Johnson, H. Serrano, C. P. Whitman, Biochemistry 2007, 46, 9596.
27. J. Rétey, K. Bartl, E. Ripp, W. E. Hull, Eur. J. Biochem. 1977, 72, 251.
28. E. Rosengren, P. Aman, S. Thelin, C. Hansson, S. Ahlfors, P. Björk, L. Jacobsson, H. Rorsman, FEBS Lett. 1997, 417, 85.
29. J. Clardy, M. A. Fischbach, C. T. Walsh, Nat. Biotechnol. 2006, 24, 1541.
30. R. H. Baltz, Nat. Biotechnol. 2006, 24, 1533.
31. J. Y. Ho, Y. T. Huang, C. J. Wu, Y. S. Li, M. D. Tsai, T. L. Li, J. Am. Chem. Soc. 2006, 128, 13694.
32. Y. S. Li, J. Y. Ho, C. C. Huang, S. Y. Lyu, C. Y. Lee, Y. T. Huang, C. J. Wu, H. C. Chan, C. J. Huang, N. S. Hsu, M. D. Tsai, T. L. Li, J. Am. Chem. Soc. 2007, 129, 13384.
33. P. Goldman, P. R. Vagelos, J. Biol. Chem. 1961, 236, 2620.
34. D. Spiteller, W. Boland, J. Org. Chem. 2003, 68, 8743.
35. M. J. Todd, J. Gomez, Anal. Biochem. 2001, 296, 179.