Pseudotheonamides, serine protease inhibitors from the marine sponge Theonella swinhoei

Youichi Nakao, Akito Masuda, Shigeki Matsunaga, Nobuhiro Fusetani

Research output: Contribution to journal › Article

38 Citations (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)2425-2431
Number of pages7
JournalJournal of the American Chemical Society
Volume121
Issue number11
DOIs
Publication statusPublished - 1999 Mar 24
Externally publishedYes

Fingerprint

Theonella
Stereochemistry
Serine Proteinase Inhibitors
Porifera
Serine Proteases
varespladib methyl
Peptides
Tyrosine
Degradation
cyclotheonamide A
Peptide Hydrolases

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Pseudotheonamides, serine protease inhibitors from the marine sponge Theonella swinhoei. / Nakao, Youichi; Masuda, Akito; Matsunaga, Shigeki; Fusetani, Nobuhiro.

In: Journal of the American Chemical Society, Vol. 121, No. 11, 24.03.1999, p. 2425-2431.

Research output: Contribution to journal › Article

Nakao, Y, Masuda, A, Matsunaga, S & Fusetani, N 1999, 'Pseudotheonamides, serine protease inhibitors from the marine sponge Theonella swinhoei', Journal of the American Chemical Society, vol. 121, no. 11, pp. 2425-2431. https://doi.org/10.1021/ja9831195
Nakao Y, Masuda A, Matsunaga S, Fusetani N. Pseudotheonamides, serine protease inhibitors from the marine sponge Theonella swinhoei. Journal of the American Chemical Society. 1999 Mar 24;121(11):2425-2431. https://doi.org/10.1021/ja9831195
Nakao, Youichi ; Masuda, Akito ; Matsunaga, Shigeki ; Fusetani, Nobuhiro. / Pseudotheonamides, serine protease inhibitors from the marine sponge Theonella swinhoei. In: Journal of the American Chemical Society. 1999 ; Vol. 121, No. 11. pp. 2425-2431.
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