Biosynthesis of the bicyclic depsipeptide salinamide A in streptomyces sp. CNB-091: Origin of the carbons

Tetrahedron Letters

Volumn 39, Issue 23, 1998, Pages 3915-3918

  Moore, Bradley S ^a   Seng, Dieter ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CARBON 13; DEPSIPEPTIDE; SALINAMIDE A; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; STREPTOMYCES;

EID: 0032482492     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00726-6     Document Type: Article

References (14)

1. 1. A preliminary account of this work was presented at the 4th International Marine Biotechnology Conference, Sorrento, Italy, September 22-29, 1997. B. S. Moore, in New Developments in Marine Biotechnology, ed. Y. Le Gal and H. Halvorson, Plenum Press, in press.
2. 2. Trischman, J. A.; Tapiolas, D. M.; Jensen, P. R.; Fenical, W.; McKee, T. C.; Ireland, C. M.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1994, 116, 757-758.
3. 3. Moore, B. S.; Trischman, J. A.; Seng, D.; Kho, D.; Jensen, P. R.; Fenical, W., submitted.
4. 4. Miao, S.; Anstee, M. R.; LaMarco, K.; Matthew, J.; Huang, L. H. T.; Brasseur, M. M. J. Nat. Prod. 1997, 60, 858-861.
5. 5. For excellent reviews on multifunctional peptide synthetases involved in nonribosomal peptide synthesis see: Marahiel, M. A.; Stachelhaus, T.; Mootz, H. D. Chem. Rev. 1997, 97, 2651-2673; von Döhren, H.; Keller, U.; Vater, J.; Zocher, R. Chem. Rev. 1997, 97, 2675-2705.
6. 5. For excellent reviews on multifunctional peptide synthetases involved in nonribosomal peptide synthesis see: Marahiel, M. A.; Stachelhaus, T.; Mootz, H. D. Chem. Rev. 1997, 97, 2651-2673; von Döhren, H.; Keller, U.; Vater, J.; Zocher, R. Chem. Rev. 1997, 97, 2675-2705.
7. 6. In Nocardia uniformis subsp. tsuyamanensis, the Hpg residue in the monocyclic β-lactam antibiotic nocardicin A is derived from tyrosine. Townsend, C. A.; Brown, A. M. J. Am. Chem. Soc. 1983, 105, 913-918.
8. 7. Reynolds, K. A.; O'Hagan, D.; Gani, D.; Robinson, J. A. J. Chem. Soc. Perkin Trans I 1988, 3195-3207.
9. 8. Such CoA mimics have been shown in the past to be more efficiently incorporated than the free acids due to their presumed more facile transesterification with a thiol group on an enzyme. Yue, S.; Duncan, J. S.; Yamamoto, Y.; Hutchinson, C. R. J. Am. Chem. Soc. 1987, 109, 1253-1255;
10. Cane, D. E.; Yang, C.-C. J. Am. Chem. Soc. 1987, 109, 1255-1257.
11. 9. The NAC thioester 6b was prepared from the 6a acid anhydride and the thallium salt of NAC according to Schwab, J. M.; Klassen, J. B. J. Am. Chem. Soc. 1984, 106, 7217-7227.
12. 10. Such Fe(II)-dependent oxygenase reactions have precedence in β-lactam chemistry and have also been proposed to account for polyether formation in polyketides such as monensin and brevetoxin. Townsend, C. A.; Basak, A. Tetrahedron 1991, 47, 2591-2602.
13. 11. Direct conversion of an alcohol to an epoxide via a dehydrogenation reaction has precedence in scopolamine (Hashimoto, T.; Matsuda, J.; Yamada, Y. FEBS Lett. 1993, 329, 35-39) and fosfomycin
14. (Seto, H.; Hidaka, T.; Kuzuyama, T.; Shibahara, S.; Usui, T.; Sakanaka, O.; Imai, S. J. Antibiot. 1991, 44, 1286-1288) biosynthesis.