Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 3, Pages 1156-1162Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo8022582
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Funding
- NIH [RR13030, RR06262, RR14768, CA36622]
- NSF [DBI-0002806]
- NCI [CA67786]
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Eudistomides A (1) and B (2), two new cyclic peptides, were isolated from a Fijian ascidian Eudistoma sp. These five-residue cystine-linked cyclic peptides are flanked by a C-terminal methyl ester and a 12-oxo- or 12-hydroxy-tetradecanoyl moiety. The complete structures of the eudistomides were determined using a combination of spectroscopic and chemical methods. Chiral HPLC analysis revealed that all five amino acid residues in 1 and 2 had the L-configuration. Total synthesis of eudistomides A (1) and B (2) confirmed the proposed structures. Enantioselective lipase-catalyzed hydrolysis of a mixture of C-35 acetoxy epimers indicated a 35R absolute configuration for 2.
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