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 language | English |
|---|---|
| Pages (from-to) | 2425-2431 |
| Number of pages | 7 |
| Journal | Journal of the American Chemical Society |
| Volume | 121 |
| Issue number | 11 |
| DOIs | |
| Publication status | Published - 1999 Mar 24 |
| Externally published | Yes |
Fingerprint
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
}
TY - JOUR
T1 - Pseudotheonamides, serine protease inhibitors from the marine sponge Theonella swinhoei
AU - Nakao, Youichi
AU - Masuda, Akito
AU - Matsunaga, Shigeki
AU - Fusetani, Nobuhiro
PY - 1999/3/24
Y1 - 1999/3/24
N2 - 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).
AB - 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).
UR - http://www.scopus.com/inward/record.url?scp=0033599492&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0033599492&partnerID=8YFLogxK
U2 - 10.1021/ja9831195
DO - 10.1021/ja9831195
M3 - Article
AN - SCOPUS:0033599492
VL - 121
SP - 2425
EP - 2431
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 11
ER -