Talauxins

hybrid phenalenone dimers from Talaromyces stipitatus

Nirmal K. Chaudhary, Andrew Crombie, Daniel Vuong, Ernest Lacey, Andrew M. Piggott, Peter Karuso*

*Corresponding author for this work

Research output: Contribution to journalArticle

Abstract

Cultivation and extraction of the fungus Talaromyces stipitatus led to the isolation of five new oxyphenalenone-amino acid hybrids, which were named talauxins E, Q, V, L, and I based on the corresponding one-letter amino acid codes, along with their putative biosynthetic precursor, duclauxin. The rapid reaction of duclauxin with amino acids to produce talauxins was demonstrated in vitro and exploited to generate a small library of natural and unnatural talauxins. Talauxin V was shown to undergo spontaneous elimination of methyl acetate to yield the corresponding neoclauxin scaffold. This process was modeled using density functional theory calculations, revealing a dramatic change in conformation resulting from the syn elimination of methyl acetate.

Original languageEnglish
Pages (from-to)1051-1060
Number of pages10
JournalJournal of Natural Products
Volume83
Issue number4
Early online date2 Mar 2020
DOIs
Publication statusPublished - 24 Apr 2020

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