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Volumn 33, Issue 10, 2004, Pages 1262-1263

Spongiacysteine, a novel cysteine derivative from marine sponge Spongia sp.

Author keywords

[No Author keywords available]

Indexed keywords

BLASTICIDIN S; CYSTEINE DERIVATIVE; KASUGAMYCIN; SPONGIACYSTEINE; UNCLASSIFIED DRUG;

EID: 11844254446     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.1262     Document Type: Article
Times cited : (13)

References (17)
  • 2
    • 11844278161 scopus 로고    scopus 로고
    • note
    • This sponge was identified as a new species in Spongia by Professor Patricia R. Bergquist, the University of Auckland.
  • 3
    • 11844291882 scopus 로고    scopus 로고
    • note
    • -1.
  • 6
    • 0028332522 scopus 로고
    • In the modified Mosher's method, the effects of a MTPA ester were thought to appear more strongly at the γ- and ε-hydrogens than at the β- and δ-hydrogens in acyclic compounds. In spongiacysteine (1), we could conclude that H-4 was strongly influenced by the MTPA ester at C-2. On the other hand, H-3 was influenced by the MTPA ester at C-5. The positional differences of the effect of the MTPA group are found in many literatures. See: T. Kusumi, T. Ooi, and H. Uchimura, Tetrahedron Lett., 35, 3127 (1994); T. Kusumi, H. Takahashi, P. Xu, T. Fukushima, Y. Asakawa, T. Hashimoto, Y. Kan, and Y. Inouye, Tetrahedron Lett., 35, 4397 (1994); K. Kouda, T. Ooi, and T. Kusumi, Tetrahedron Lett., 40, 3005 (1999).
    • (1994) Tetrahedron Lett. , vol.35 , pp. 3127
    • Kusumi, T.1    Ooi, T.2    Uchimura, H.3
  • 7
    • 0028263417 scopus 로고
    • In the modified Mosher's method, the effects of a MTPA ester were thought to appear more strongly at the γ- and ε-hydrogens than at the β- and δ-hydrogens in acyclic compounds. In spongiacysteine (1), we could conclude that H-4 was strongly influenced by the MTPA ester at C-2. On the other hand, H-3 was influenced by the MTPA ester at C-5. The positional differences of the effect of the MTPA group are found in many literatures. See: T. Kusumi, T. Ooi, and H. Uchimura, Tetrahedron Lett., 35, 3127 (1994); T. Kusumi, H. Takahashi, P. Xu, T. Fukushima, Y. Asakawa, T. Hashimoto, Y. Kan, and Y. Inouye, Tetrahedron Lett., 35, 4397 (1994); K. Kouda, T. Ooi, and T. Kusumi, Tetrahedron Lett., 40, 3005 (1999).
    • (1994) Tetrahedron Lett. , vol.35 , pp. 4397
    • Kusumi, T.1    Takahashi, H.2    Xu, P.3    Fukushima, T.4    Asakawa, Y.5    Hashimoto, T.6    Kan, Y.7    Inouye, Y.8
  • 8
    • 0033537913 scopus 로고    scopus 로고
    • In the modified Mosher's method, the effects of a MTPA ester were thought to appear more strongly at the γ- and ε-hydrogens than at the β- and δ-hydrogens in acyclic compounds. In spongiacysteine (1), we could conclude that H-4 was strongly influenced by the MTPA ester at C-2. On the other hand, H-3 was influenced by the MTPA ester at C-5. The positional differences of the effect of the MTPA group are found in many literatures. See: T. Kusumi, T. Ooi, and H. Uchimura, Tetrahedron Lett., 35, 3127 (1994); T. Kusumi, H. Takahashi, P. Xu, T. Fukushima, Y. Asakawa, T. Hashimoto, Y. Kan, and Y. Inouye, Tetrahedron Lett., 35, 4397 (1994); K. Kouda, T. Ooi, and T. Kusumi, Tetrahedron Lett., 40, 3005 (1999).
    • (1999) Tetrahedron Lett. , vol.40 , pp. 3005
    • Kouda, K.1    Ooi, T.2    Kusumi, T.3
  • 11
    • 11844251099 scopus 로고    scopus 로고
    • note
    • 3, 3H), 2.72 (dd, J = 2.6, 15.3 Hz, H-3′β, 1H), 2.28 (dd, J = 6.9, 14.8 Hz, H-2″α, 1H), 2.22 (dd, J = 6.8, 14.8 Hz, H-2″β, 1H), 2.17 (m, H-3″, 1H), 1.65-1.20 (m, H-4, H-6, H-7, 6H), 1.45 (d, J = 6.3 Hz, H-1, 3H), 0.98 (d, J = 6.4 Hz, H-4″, 3H), 0.97 (d, J = 6.4 Hz, H-5″, 3H), 0.93 (t, J = 7.1 Hz, H-8, 3H).
  • 16
    • 11844296603 scopus 로고    scopus 로고
    • note
    • D -115 (c 0.02, MeOH). The difference in the values between the natural and synthetic samples may be due to an error in the measurement of the natural specimen due to lack of the sample.


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