Revised absolute stereochemistry of natural kulokekahilide-2

Yuuki Takada; Masahiro Umehara; Yoichi Nakao; Junji Kimura

doi:10.1016/j.tetlet.2007.12.050

Revised absolute stereochemistry of natural kulokekahilide-2

Yuuki Takada, Masahiro Umehara, Yoichi Nakao, Junji Kimura

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

Kulokekahilide-2 is a potent cytotoxic depsipeptide isolated from the Hawaiian marine mollusk Philinopsis speciosa. The structure of kulokekahilide-2 was reported to be composed of five amino acids (l-Ala, l-Ile, MeGly, l-MePhe, d-Ala) and two hydroxy acids (d-Hica, 5S,6S,7S-Dtda); however, following its total synthesis, the ¹H NMR spectrum of the synthetic compound was found to be different from that of the natural one, suggesting that the stereochemistry of the reported structure was incorrect. To determine the stereochemistry of the natural compound, arrays of analogues have been prepared using different sets of chiral amino acids, and the absolute stereochemistry of kulokekahilide-2 has been unambiguously confirmed to involve the combination 21-l-Ala, 24-d-MePhe, and 43-d-Ala.

Original language	English
Pages (from-to)	1163-1165
Number of pages	3
Journal	Tetrahedron Letters
Volume	49
Issue number	7
DOIs	https://doi.org/10.1016/j.tetlet.2007.12.050
Publication status	Published - 2008 Feb 11

Keywords

Cytotoxicity
Kulokekahilide-2
Macrolactamization
cis-trans Conformations

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Revised absolute stereochemistry of natural kulokekahilide-2",

abstract = "Kulokekahilide-2 is a potent cytotoxic depsipeptide isolated from the Hawaiian marine mollusk Philinopsis speciosa. The structure of kulokekahilide-2 was reported to be composed of five amino acids (l-Ala, l-Ile, MeGly, l-MePhe, d-Ala) and two hydroxy acids (d-Hica, 5S,6S,7S-Dtda); however, following its total synthesis, the 1H NMR spectrum of the synthetic compound was found to be different from that of the natural one, suggesting that the stereochemistry of the reported structure was incorrect. To determine the stereochemistry of the natural compound, arrays of analogues have been prepared using different sets of chiral amino acids, and the absolute stereochemistry of kulokekahilide-2 has been unambiguously confirmed to involve the combination 21-l-Ala, 24-d-MePhe, and 43-d-Ala.",

keywords = "Cytotoxicity, Kulokekahilide-2, Macrolactamization, cis-trans Conformations",

author = "Yuuki Takada and Masahiro Umehara and Yoichi Nakao and Junji Kimura",

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doi = "10.1016/j.tetlet.2007.12.050",

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AU - Takada, Yuuki

AU - Umehara, Masahiro

AU - Nakao, Yoichi

AU - Kimura, Junji

PY - 2008/2/11

Y1 - 2008/2/11

N2 - Kulokekahilide-2 is a potent cytotoxic depsipeptide isolated from the Hawaiian marine mollusk Philinopsis speciosa. The structure of kulokekahilide-2 was reported to be composed of five amino acids (l-Ala, l-Ile, MeGly, l-MePhe, d-Ala) and two hydroxy acids (d-Hica, 5S,6S,7S-Dtda); however, following its total synthesis, the 1H NMR spectrum of the synthetic compound was found to be different from that of the natural one, suggesting that the stereochemistry of the reported structure was incorrect. To determine the stereochemistry of the natural compound, arrays of analogues have been prepared using different sets of chiral amino acids, and the absolute stereochemistry of kulokekahilide-2 has been unambiguously confirmed to involve the combination 21-l-Ala, 24-d-MePhe, and 43-d-Ala.

AB - Kulokekahilide-2 is a potent cytotoxic depsipeptide isolated from the Hawaiian marine mollusk Philinopsis speciosa. The structure of kulokekahilide-2 was reported to be composed of five amino acids (l-Ala, l-Ile, MeGly, l-MePhe, d-Ala) and two hydroxy acids (d-Hica, 5S,6S,7S-Dtda); however, following its total synthesis, the 1H NMR spectrum of the synthetic compound was found to be different from that of the natural one, suggesting that the stereochemistry of the reported structure was incorrect. To determine the stereochemistry of the natural compound, arrays of analogues have been prepared using different sets of chiral amino acids, and the absolute stereochemistry of kulokekahilide-2 has been unambiguously confirmed to involve the combination 21-l-Ala, 24-d-MePhe, and 43-d-Ala.

KW - Cytotoxicity

KW - Kulokekahilide-2

KW - Macrolactamization

KW - cis-trans Conformations

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JF - Tetrahedron Letters

SN - 0040-4039

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Revised absolute stereochemistry of natural kulokekahilide-2

Abstract

Keywords

ASJC Scopus subject areas

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