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

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

Research output: Contribution to journalArticle

28 Citations (Scopus)

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
Externally publishedYes

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biosynthesis
Biosynthesis
Sirolimus
Carboxylic Acids
Sulfur
carboxylic acids
sulfur
analogs
Streptomyces
Immunosuppressive Agents
Biological Products
acids
products
matrices
compound 20
nipecotic acid

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Graziani, E. I., Ritacco, F. V., Summers, M. Y., Zabriskie, M., Yu, K., Bernan, V. S., ... 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

Novel sulfur-containing rapamycin analogs prepared by precursor-directed biosynthesis. / Graziani, Edmund I.; Ritacco, Frank V.; Summers, Mia Y.; Zabriskie, Mark; Yu, Ker; Bernan, Valerie S.; Greenstein, Michael; Carter, Guy T.

In: Organic Letters, Vol. 5, No. 14, 10.07.2003, p. 2385-2388.

Research output: Contribution to journalArticle

Graziani, EI, Ritacco, FV, Summers, MY, Zabriskie, M, Yu, K, Bernan, VS, Greenstein, M & Carter, GT 2003, 'Novel sulfur-containing rapamycin analogs prepared by precursor-directed biosynthesis', Organic Letters, vol. 5, no. 14, pp. 2385-2388. https://doi.org/10.1021/ol034591k
Graziani, Edmund I. ; Ritacco, Frank V. ; Summers, Mia Y. ; Zabriskie, Mark ; Yu, Ker ; Bernan, Valerie S. ; Greenstein, Michael ; Carter, Guy T. / Novel sulfur-containing rapamycin analogs prepared by precursor-directed biosynthesis. In: Organic Letters. 2003 ; Vol. 5, No. 14. pp. 2385-2388.
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AU - Bernan, Valerie S.

AU - Greenstein, Michael

AU - Carter, Guy T.

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