Novel sulfur-containing rapamycin analogs prepared by precursor-directed biosynthesis

Edmund I. Graziani, Frank V. Ritacco, Mia Y. Summers, T. Mark Zabriskie, Ker Yu, Valerie S. Bernan, Michael Greenstein, Guy T. Carter

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29 Scopus citations

Abstract

(Matrix presented) Two novel sulfur-containing analogs of the immunosuppressive natural product rapamycin (1) were obtained by feeding cultures of Streptomyces hygroscopicus with L-nipecotic acid (4) and either (S)-1,3-thiazane-4-carboxylic acid (5) or (S)-1,4-thiazane-3-carboxylic acid (6). The structures of the two new compounds, 20-thiarapamycin (2) and 15-deoxo-19-sulfoxylrapamycin (3), were determined by spectroscopic methods.

Original languageEnglish (US)
Pages (from-to)2385-2388
Number of pages4
JournalOrganic Letters
Volume5
Issue number14
DOIs
StatePublished - Jul 10 2003

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Graziani, E. I., Ritacco, F. V., Summers, M. Y., Zabriskie, T. M., Yu, K., Bernan, V. S., Greenstein, M., & Carter, G. T. (2003). Novel sulfur-containing rapamycin analogs prepared by precursor-directed biosynthesis. Organic Letters, 5(14), 2385-2388. https://doi.org/10.1021/ol034591k