Biosynthesis of Athmu, a alpha,gamma-hydroxy-ß-amino acid of pahayokolides A-B

Published

October 2, 2012

Author(s)

Li Liu, Dan Bearden, Juan C. Rodriguez, Kathleen S. Rein

Abstract

Pahayokolides A-B are cyanobacteria derived non-ribosomal peptides which exhibit cytotoxicity against a number of cancer cell lines. The biosynthetic origin of the 3-amino-2,5,7,8- tetrahydroxy-10-methylundecanoic acid (Athmu) moiety has been investigated using stable isotope incorporation experiments. While α-ketoisocaproic acid (α-KIC), α-hydroxyisocaproic acid (α- HIC) and leucine all serve as precursors to Athmu, the feeding of [1-13C] α-KIC results in more than threefold greater 13C enrichment than the other precursors. This result suggests that α-KIC is the immediate precursor which is selected and activated by the adenylation domain of the loading NRPS module and subsequently reduced in a fashion similar to that of the recently identified pathways for cryptophycins A-B, cereulide and valinomycin.

Citation

Tetrahedron Letters

Volume

53

Pub Type

Journals

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DOI Link

Keywords

NMR, Pahayokolide, Biosynthesis

Citation

Liu, L. , Bearden, D. , Rodriguez, J. and Rein, K. (2012), Biosynthesis of Athmu, a alpha,gamma-hydroxy-ß-amino acid of pahayokolides A-B, Tetrahedron Letters, [online], https://doi.org/10.1016/j.tetlet.2012.09.119 (Accessed October 12, 2025)