Total synthesis and conformational studies of ceratospongamide, a bioactive cyclic heptapeptide from marine origin
Тип публикации: Journal Article
Дата публикации: 2002-09-01
SCImago Q3
WOS Q3
БС2
SJR: 0.36
CiteScore: 3.7
Impact factor: 2.1
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
The first total synthesis of cis,cis-ceratospongamide (cyclo[ l -Pro- l -Ile-Me-oxazoline- l -Phe- l -Pro-thiazole- l -Phe-]) was accomplished and confirmed by X-ray crystal analysis. The heating of cis,cis-ceratospongamide in DMSO converted it not to the trans,trans isomer but to the trans,trans-[ d -allo-Ile]-ceratospongamide, which was confirmed by total synthesis. Its solution conformation was constructed by the dynamic simulated annealing method using ROE cross peaks, revealing a rounded and flat ring structure which is in contrast with the slim and tight structure of cis,cis isomer. The results shows that the trans,trans-[ d -allo-Ile] isomer is the main thermal product of cis,cis-ceratospongamide.
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ГОСТ
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Yokokawa F. et al. Total synthesis and conformational studies of ceratospongamide, a bioactive cyclic heptapeptide from marine origin // Tetrahedron. 2002. Vol. 58. No. 40. pp. 8127-8143.
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Yokokawa F., Sameshima H., In Y., Minoura K., Ishida T., Shioiri T. Total synthesis and conformational studies of ceratospongamide, a bioactive cyclic heptapeptide from marine origin // Tetrahedron. 2002. Vol. 58. No. 40. pp. 8127-8143.
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TY - JOUR
DO - 10.1016/S0040-4020(02)00906-7
UR - https://doi.org/10.1016/S0040-4020(02)00906-7
TI - Total synthesis and conformational studies of ceratospongamide, a bioactive cyclic heptapeptide from marine origin
T2 - Tetrahedron
AU - Yokokawa, Fumiaki
AU - Sameshima, Hirofumi
AU - In, Yasuko
AU - Minoura, Katsuhiko
AU - Ishida, Toshimasa
AU - Shioiri, Takayuki
PY - 2002
DA - 2002/09/01
PB - Elsevier
SP - 8127-8143
IS - 40
VL - 58
SN - 0040-4020
SN - 1464-5416
ER -
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@article{2002_Yokokawa,
author = {Fumiaki Yokokawa and Hirofumi Sameshima and Yasuko In and Katsuhiko Minoura and Toshimasa Ishida and Takayuki Shioiri},
title = {Total synthesis and conformational studies of ceratospongamide, a bioactive cyclic heptapeptide from marine origin},
journal = {Tetrahedron},
year = {2002},
volume = {58},
publisher = {Elsevier},
month = {sep},
url = {https://doi.org/10.1016/S0040-4020(02)00906-7},
number = {40},
pages = {8127--8143},
doi = {10.1016/S0040-4020(02)00906-7}
}
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MLA
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Yokokawa, Fumiaki, et al. “Total synthesis and conformational studies of ceratospongamide, a bioactive cyclic heptapeptide from marine origin.” Tetrahedron, vol. 58, no. 40, Sep. 2002, pp. 8127-8143. https://doi.org/10.1016/S0040-4020(02)00906-7.
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