Kulokekahilide-1, a cytotoxic depsipeptide from the cephalaspidean mollusk Philinopsis speciosa

Junji Kimura; Yuuki Takada; Tomoko Inayoshi; Yoichi Nakao; Gilles Goetz; Wesley Y. Yoshida; Paul J. Scheuer

doi:10.1021/jo010176z

Kulokekahilide-1, a cytotoxic depsipeptide from the cephalaspidean mollusk Philinopsis speciosa

Junji Kimura, Yuuki Takada, Tomoko Inayoshi, Yoichi Nakao, Gilles Goetz, Wesley Y. Yoshida, Paul J. Scheuer^*

^*この研究の対応する著者

研究成果: Article › 査読

60 被引用数 (Scopus)

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The cytotoxic depsipeptide kulokekahilide-1, which contains two unusual amino acids, 4-phenylvaline and 3-amino-2-methylhexanoic acid, was isolated from the cephalaspidean mollusk Philinopsis speciosa. Structure elucidation of kulokekahilide-1 was carried out by spectroscopic analysis and chemical degradation. The absolute stereochemistry was determined by Marfey analysis for amino acids and chiral HPLC analysis for hydroxy acids. All four stereoisomers of 4-phenylvaline and 3-amino-2-methylhexanoic acid, which were necessary for Marfey analysis, were synthesized by use of the Heck reaction and Evans's method, respectively. Kulokekahilide-1 showed cytotoxicity against P388 murine leukemia cells with an IC₅₀ value of 2.1 μg/mL.

本文言語	English
ページ（範囲）	1760-1767
ページ数	8
ジャーナル	Journal of Organic Chemistry
巻	67
号	6
DOI	https://doi.org/10.1021/jo010176z
出版ステータス	Published - 2002 3月 22
外部発表	はい

ASJC Scopus subject areas

有機化学

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title = "Kulokekahilide-1, a cytotoxic depsipeptide from the cephalaspidean mollusk Philinopsis speciosa",

abstract = "The cytotoxic depsipeptide kulokekahilide-1, which contains two unusual amino acids, 4-phenylvaline and 3-amino-2-methylhexanoic acid, was isolated from the cephalaspidean mollusk Philinopsis speciosa. Structure elucidation of kulokekahilide-1 was carried out by spectroscopic analysis and chemical degradation. The absolute stereochemistry was determined by Marfey analysis for amino acids and chiral HPLC analysis for hydroxy acids. All four stereoisomers of 4-phenylvaline and 3-amino-2-methylhexanoic acid, which were necessary for Marfey analysis, were synthesized by use of the Heck reaction and Evans's method, respectively. Kulokekahilide-1 showed cytotoxicity against P388 murine leukemia cells with an IC50 value of 2.1 μg/mL.",

author = "Junji Kimura and Yuuki Takada and Tomoko Inayoshi and Yoichi Nakao and Gilles Goetz and Yoshida, {Wesley Y.} and Scheuer, {Paul J.}",

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AU - Kimura, Junji

AU - Takada, Yuuki

AU - Inayoshi, Tomoko

AU - Nakao, Yoichi

AU - Goetz, Gilles

AU - Yoshida, Wesley Y.

AU - Scheuer, Paul J.

PY - 2002/3/22

Y1 - 2002/3/22

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AB - The cytotoxic depsipeptide kulokekahilide-1, which contains two unusual amino acids, 4-phenylvaline and 3-amino-2-methylhexanoic acid, was isolated from the cephalaspidean mollusk Philinopsis speciosa. Structure elucidation of kulokekahilide-1 was carried out by spectroscopic analysis and chemical degradation. The absolute stereochemistry was determined by Marfey analysis for amino acids and chiral HPLC analysis for hydroxy acids. All four stereoisomers of 4-phenylvaline and 3-amino-2-methylhexanoic acid, which were necessary for Marfey analysis, were synthesized by use of the Heck reaction and Evans's method, respectively. Kulokekahilide-1 showed cytotoxicity against P388 murine leukemia cells with an IC50 value of 2.1 μg/mL.

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Kulokekahilide-1, a cytotoxic depsipeptide from the cephalaspidean mollusk Philinopsis speciosa

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