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

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Author(s): Li Liu; Daniel W. Bearden; Juan C. Rodriguez; Kathleen S. Rein;
Title: Biosynthesis of Athmu, a alpha,gamma-hydroxy-ß-amino acid of pahayokolides A-B
Published: October 02, 2012
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
Pages: pp. 6758 - 6760
Keywords: NMR, Pahayokolide, Biosynthesis
Research Areas: NMR, Organic Analytical Chemistry, Chemistry
DOI: http://dx.doi.org/10.1016/j.tetlet.2012.09.119  (Note: May link to a non-U.S. Government webpage)