Total Synthesis of Alloviroidin

Carol M. Taylor, Samuel K. Kutty, Benson J. Edagwa

Research output: Contribution to journalArticlepeer-review

Abstract

Alloviroidin is a cyclic heptapeptide, produced by several species of Amanita mushrooms, that demonstrates high affinity for F-actin as is characteristic of virotoxins and phallotoxins. Alloviroidin was synthesized via a [3 + 4] fragment condensation of Fmoc-d-Thr(OTBS)-d-Ser(OTBS)-(2S,3R,4R)-DHPro(OTBS) 2 -OH and H-Ala-Trp(2-SO 2 Me)-(2S,4S)-DHLeu(5-OTBS)-Val-OMe to form bond A. The linear heptapeptide favored a turn conformation, facilitating cyclization between Val 1 and d-Thr 2 (position B). Global deprotection and HPLC purification afforded alloviroidin with NMR spectra in excellent agreement with the natural product.

Original languageEnglish (US)
Pages (from-to)2281-2284
Number of pages4
JournalOrganic Letters
Volume21
Issue number7
DOIs
StatePublished - Apr 5 2019

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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