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 | |
| Publication status | Published - 2008 Feb 11 |
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Keywords
- cis-trans Conformations
- Cytotoxicity
- Kulokekahilide-2
- Macrolactamization
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Revised absolute stereochemistry of natural kulokekahilide-2. / Takada, Yuuki; Umehara, Masahiro; Nakao, Youichi; Kimura, Junji.
In: Tetrahedron Letters, Vol. 49, No. 7, 11.02.2008, p. 1163-1165.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Revised absolute stereochemistry of natural kulokekahilide-2
AU - Takada, Yuuki
AU - Umehara, Masahiro
AU - Nakao, Youichi
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 - cis-trans Conformations
KW - Cytotoxicity
KW - Kulokekahilide-2
KW - Macrolactamization
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U2 - 10.1016/j.tetlet.2007.12.050
DO - 10.1016/j.tetlet.2007.12.050
M3 - Article
VL - 49
SP - 1163
EP - 1165
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 7
ER -