Complestatin to chloropeptin I via a quantitative acid catalyzed rearrangement. Absolute stereochemical determination of complestatin

  • Jayasuriya H
  • Salituro G
  • Smith S
 et al. 
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Abstract

Complestatin and isomeric chloropeptin I are bicyclo hexapeptides isolated from a Streptomyces sp. Both of these compounds are inhibitors of gp120-CD4 HIV fusion activity. In this paper, we describe an efficient acid catalyzed conversion of complestatin to chloropeptin I, provide a plausible mechanism for this transformation, and unambiguously assign the stereochemistry of complestatin.

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Authors

  • Hiranthi Jayasuriya

  • Gino M. Salituro

  • Scott K. Smith

  • James V. Heck

  • Steven J. Gould

  • Sheo B. Singh

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