Revised
Structure of Cyclolithistide A, a Cyclic Depsipeptide
from the Marine Sponge <i>Discodermia japonica</i>
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Abstract
A cyclic peptide was isolated from
the deep-sea marine sponge <i>Discodermia japonica</i>,
and its NMR spectroscopic data were
identical to those reported for cyclolithistide A, a known antifungal
depsipeptide. However, the interresidue HMBC correlations suggested
that the amino acid sequence was different from that of the original
structure. Moreover, chiral-phase GC-MS, combined with Marfey’s
analysis, indicated that the absolute configurations of three amino
acids were also antipodal. Here, we propose the revised structure
of cyclolithistide A and address the configuration of the previously
unassigned 4-amino-3,5-dihydroxyhexanoic acid (Adha) moiety