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



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


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.
Tetrahedron Letters


NMR, Pahayokolide, Biosynthesis


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], (Accessed June 19, 2024)


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Created October 1, 2012, Updated October 12, 2021