Total Synthesis of Alloviroidin

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

Research output: Contribution to journalArticle

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

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purification
affinity
condensation
fragments
alanyl-tryptophyl-alanine
nuclear magnetic resonance
synthesis
products
Amanita
Agaricales
Cyclization
Biological Products
Purification
Conformations
Actins
Condensation
High Pressure Liquid Chromatography
Nuclear magnetic resonance
viroidin

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Total Synthesis of Alloviroidin. / Taylor, Carol M.; Kutty, Samuel K.; Edagwa, Benson J.

In: Organic Letters, Vol. 21, No. 7, 05.04.2019, p. 2281-2284.

Research output: Contribution to journalArticle

Taylor, Carol M. ; Kutty, Samuel K. ; Edagwa, Benson J. / Total Synthesis of Alloviroidin. In: Organic Letters. 2019 ; Vol. 21, No. 7. pp. 2281-2284.
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