Isolation, Structure Elucidation, and Synthesis of Eudistomides A and B, Lipopeptides from a Fijian Ascidian Eudistoma sp.

作者：Whitson Emily L; Ratnayake Anokha S; Bugni Tim S; Harper Mary Kay; Ireland Chris M^*

来源：Journal of Organic Chemistry, 2009, 74(3): 1156-1162.

DOI：10.1021/jo8022582

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.

• 出版日期2009-2-6