Pseudotheonamides, Serine Protease Inhibitors from the Marine Sponge Theonella swinhoei 1

Six new peptides with serine protease inhibitory activity have been isolated from the marine sponge Theonella swinhoei. Their structures including absolute stereochemistry were unambiguously established by interpretation of spectral data and chemical degradation. Pseudotheonamides A1 (1), A2 (2), an...

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Bibliographic Details
Published in:Journal of the American Chemical Society 1999-03, Vol.121 (11), p.2425-2431
Main Authors: Nakao, Yoichi, Masuda, Akito, Matsunaga, Shigeki, Fusetani, Nobuhiro
Format: Article
Language:English
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Summary:Six new peptides with serine protease inhibitory activity have been isolated from the marine sponge Theonella swinhoei. Their structures including absolute stereochemistry were unambiguously established by interpretation of spectral data and chemical degradation. Pseudotheonamides A1 (1), A2 (2), and B2 (3) are linear pentapeptides embracing the rare piperazinone and piperidinoiminoimidazolone ring systems. Pseudotheonamide C (4) contains v-Tyr (vinylogous tyrosine) instead of a piperazinone ring. Pseudotheonamide D (5) is a tetrapeptide which lacks a C-terminal k-Arg (α-ketohomoarginine) unit. Dihydrocyclotheonamide A (6) is a reduction product of the known cyclotheonamide A (7).
ISSN:0002-7863
1520-5126
DOI:10.1021/ja9831195