Dual carbamoylations on the polyketide and glycosyl moiety by Asm21 result in extended ansamitocin biosynthesis

Chemistry and Biology

Volumn 18, Issue 12, 2011, Pages 1571-1580

  Li, Yan ^a   Zhao, Peiji ^b   Kang, Qianjin ^a   Ma, Juan ^b   Bai, Linquan ^a   Deng, Zixin ^a  

^a Shanghai Jiao Tong University   (China)

^b KUNMING INSTITUTE OF BOTANY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANSAMITOCINS; DRUG DERIVATIVE; MAYTANSINE; POLYKETIDE; TRANSFERASE;

ACTINOMYCETALES; ARTICLE; BIOCATALYSIS; BIOSYNTHESIS; CHEMISTRY; ENZYMOLOGY; GENETICS; METABOLISM; MUTATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ACTINOMYCETALES; BIOCATALYSIS; CARBOXYL AND CARBAMOYL TRANSFERASES; MAGNETIC RESONANCE SPECTROSCOPY; MAYTANSINE; MUTATION; POLYKETIDES;

ACTINOSYNNEMA PRETIOSUM;

EID: 84555202444     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2011.11.007     Document Type: Article

References (33)

1. S.J. Brewer, P.M. Taylor, and M.K. Turner An adenosine triphosphate-dependent carbamoylphosphate - 3-hydroxymethylcephem O-carbamoyltransferase from Streptomyces clavuligerus Biochem. J. 185 1980 555 564 (Pubitemid 10105225)
2. J.M. Cassady, K.K. Chan, H.G. Floss, and E. Leistner Recent developments in the maytansinoid antitumor agents Chem. Pharm. Bull. (Tokyo) 52 2004 1 26 (Pubitemid 41685545)
3. R.V. Chari Targeted cancer therapy: conferring specificity to cytotoxic drugs Acc. Chem. Res. 41 2008 98 107
4. J.C. Eads, M. Beeby, G. Scapin, T.W. Yu, and H.G. Floss Crystal structure of 3-amino-5-hydroxybenzoic acid (AHBA) synthase Biochemistry 38 1999 9840 9849
5. R.H. Flatman, A. Eustaquio, S.M. Li, L. Heide, and A. Maxwell Structure-activity relationships of aminocoumarin-type gyrase and topoisomerase IV inhibitors obtained by combinatorial biosynthesis Antimicrob. Agents Chemother. 50 2006 1136 1142
6. H.G. Floss, T.W. Yu, and K. Arakawa The biosynthesis of 3-amino-5-hydroxybenzoic acid (AHBA), the precursor of mC7N units in ansamycin and mitomycin antibiotics: a review J. Antibiot. 64 2011 35 44
7. C.L. Freel Meyers, M. Oberthür, H. Xu, L. Heide, D. Kahne, and C.T. Walsh Characterization of NovP and NovN: completion of novobiocin biosynthesis by sequential tailoring of the noviosyl ring Angew. Chem. Int. Ed. Engl. 43 2004 67 70 (Pubitemid 38063473)
8. M. Gellert, M.H. O'Dea, T. Itoh, and J. Tomizawa Novobiocin and coumermycin inhibit DNA supercoiling catalyzed by DNA gyrase Proc. Natl. Acad. Sci. USA 73 1976 4474 4478 (Pubitemid 8013922)
9. B. Gust, G.L. Challis, K. Fowler, T. Kieser, and K.F. Chater PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin Proc. Natl. Acad. Sci. USA 100 2003 1541 1546 (Pubitemid 36254483)
10. S.F. Haydock, A.N. Appleyard, T. Mironenko, J. Lester, N. Scott, and P.F. Leadlay Organization of the biosynthetic gene cluster for the macrolide concanamycin A in Streptomyces neyagawaensis ATCC 27449 Microbiology 151 2005 3161 3169 (Pubitemid 41488901)
11. Y. He, Z. Wang, L. Bai, J. Liang, X. Zhou, and Z. Deng Two pHZ1358-derivative vectors for efficient gene knockout in streptomyces J. Microbiol. Biotechnol. 20 2010 678 682
12. E. Higashide, M. Asai, K. Ootsu, S. Tanida, Y. Kozai, T. Hasegawa, T. Kishi, Y. Sugino, and M. Yoneda Ansamitocin, a group of novel maytansinoid antibiotics with antitumour properties from Nocardia Nature 270 1977 721 722 (Pubitemid 8239243)
13. D.C. Hooper, J.S. Wolfson, G.L. McHugh, M.B. Winters, and M.N. Swartz Effects of novobiocin, coumermycin A1, clorobiocin, and their analogs on Escherichia coli DNA gyrase and bacterial growth Antimicrob. Agents Chemother. 22 1982 662 671 (Pubitemid 13206550)
14. J. Ishikawa, and K. Hotta FramePlot: a new implementation of the frame analysis for predicting protein-coding regions in bacterial DNA with a high G + C content FEMS Microbiol. Lett. 174 1999 251 253 (Pubitemid 29217014)
15. T. Kieser, M.J. Bibb, M.J. Buttner, K.F. Charter, and D.A. Hopwood Practical Streptomyces Genetics 2000 The John Innes Foundation Norwich, United Kingdom
16. H. Kinashi, K. Someno, and K. Sakaguchi Isolation and characterization of concanamycins A, B and C J. Antibiot. 37 1984 1333 1343 (Pubitemid 15220692)
17. T. Knobloch, K. Harmrolfs, F. Taft, B. Thomaszewski, F. Sasse, and A. Kirschning Mutational biosynthesis of ansamitocin antibiotics: A diversity-oriented approach to exploit biosynthetic flexibility ChemBioChem 12 2011 540 547
18. S.M. Kupchan, A.T. Sneden, A.R. Branfman, G.A. Howie, L.I. Rebhun, W.E. McIvor, R.W. Wang, and T.C. Schnaitman Structural requirements for antileukemic activity among the naturally occurring and semisynthetic maytansinoids J. Med. Chem. 21 1978 31 37
19. R.J. Lewis, O.M. Singh, C.V. Smith, T. Skarzynski, A. Maxwell, A.J. Wonacott, and D.B. Wigley The nature of inhibition of DNA gyrase by the coumarins and the cyclothialidines revealed by X-ray crystallography EMBO J. 15 1996 1412 1420 (Pubitemid 26093794)
20. C. Lu, L. Bai, and Y. Shen A novel amide N-glycoside of ansamitocins from Actinosynnema pretiosum J. Antibiot. 57 2004 348 350 (Pubitemid 38811721)
21. J. Ma, P.J. Zhao, and Y.M. Shen New amide N-glycosides of ansamitocins identified from Actinosynnema pretiosum Arch. Pharm. Res. 30 2007 670 673
22. T.W. Miller, R.T. Goegelman, R.G. Weston, I. Putter, and F.J. Wolf Cephamycins, a new family of beta-lactam antibiotics. II. Isolation and chemical characterization Antimicrob. Agents Chemother. 2 1972 132 135
23. R. Nagarajan, L.D. Boeck, M. Gorman, R.L. Hamill, C.E. Higgens, M.M. Hoehn, W.M. Stark, and J.G. Whitney Beta-lactam antibiotics from Streptomyces J. Am. Chem. Soc. 93 1971 2308 2310
24. A. Neumann, G. Wohlfarth, and G. Diekert Purification and characterization of tetrachloroethene reductive dehalogenase from Dehalospirillum multivorans J. Biol. Chem. 271 1996 16515 16519 (Pubitemid 26239004)
25. C.E. Snipes, D.O. Duebelbeis, M. Olson, D.R. Hahn, W.H. Dent 3rd, J.R. Gilbert, T.L. Werk, G.E. Davis, R. Lee-Lu, and P.R. Graupner The ansacarbamitocins: polar ansamitocin derivatives J. Nat. Prod. 70 2007 1578 1581 (Pubitemid 350155406)
26. P. Spiteller, L. Bai, G. Shang, B.J. Carroll, T.W. Yu, and H.G. Floss The post-polyketide synthase modification steps in the biosynthesis of the antitumor agent ansamitocin by Actinosynnema pretiosum J. Am. Chem. Soc. 125 2003 14236 14237 (Pubitemid 37452337)
27. M. Steffensky, A. Mühlenweg, Z.X. Wang, S.M. Li, and L. Heide Identification of the novobiocin biosynthetic gene cluster of Streptomyces spheroides NCIB 11891 Antimicrob. Agents Chemother. 44 2000 1214 1222 (Pubitemid 30228297)
28. G.Z. Wei, L.Q. Bai, T. Yang, J. Ma, Y. Zeng, Y.M. Shen, and P.J. Zhao A new antitumour ansamitocin from Actinosynnema pretiosum Nat. Prod. Res. 24 2010 1146 1150
29. Y. Wu, Q. Kang, G. Shang, P. Spiteller, B. Carroll, T.W. Yu, W. Su, L. Bai, and H.G. Floss N-methylation of the amide bond by methyltransferase asm10 in ansamitocin biosynthesis ChemBioChem 12 2011 1759 1766
30. Y. Wu, Q. Kang, Y. Shen, W. Su, and L. Bai Cloning and functional analysis of the naphthomycin biosynthetic gene cluster in Streptomyces sp. CS Mol. Biosyst. 7 2011 2459 2469
31. H. Xu, L. Heide, and S.M. Li New aminocoumarin antibiotics formed by a combined mutational and chemoenzymatic approach utilizing the carbamoyltransferase NovN Chem. Biol. 11 2004 655 662 (Pubitemid 38708834)
32. T.W. Yu, L. Bai, D. Clade, D. Hoffmann, S. Toelzer, K.Q. Trinh, J. Xu, S.J. Moss, E. Leistner, and H.G. Floss The biosynthetic gene cluster of the maytansinoid antitumor agent ansamitocin from Actinosynnema pretiosum Proc. Natl. Acad. Sci. USA 99 2002 7968 7973 (Pubitemid 34650989)
33. P. Zhao, L. Bai, J. Ma, Y. Zeng, L. Li, Y. Zhang, C. Lu, H. Dai, Z. Wu, and Y. Li Amide N-glycosylation by Asm25, an N-glycosyltransferase of ansamitocins Chem. Biol. 15 2008 863 874