The Absolute Configuration of Belactin A, a β-Lactone-Containing Serine Carboxypeptidase Inhibitor: Importance of the β-Lactone Structure for Serine Carboxypeptidase Inhibition

Shoichi Murakami Institute of Microbial Chemistry, 3-14-23 Kamiosaki, Sinagawa-ku, Tokyo, 141-0021, Japan

Yoshikazu Takahashi Institute of Microbial Chemistry, 3-14-23 Kamiosaki, Sinagawa-ku, Tokyo, 141-0021, Japan

Tomio Takeuchi Institute of Microbial Chemistry, 3-14-23 Kamiosaki, Sinagawa-ku, Tokyo, 141-0021, Japan

Yoshio Kodama Pharmaceutical Research Center, Meiji Seika Kaisha Ltd., 760 Morooka-cho, Kohoku-ku, Yokohama, 222-8567, Japan

Takaaki Aoyagi Institute of Microbial Chemistry, 3-14-23 Kamiosaki, Sinagawa-ku, Tokyo, 141-0021, Japan; Showa College of Pharmaceutical Sciences, 3-3165 Higashitamagawagakuen, Machida-shi, Tokyo, 194, Japan

Abstract

The absolute configuration of belactin A, a β-lactone-containing serine carboxypeptidase inhibitor was studied by a crystal X-ray diffraction analysis and its absolute structure was determined to be (2R,3S)-2-{(3S)-3-[(2-amino-5-chlorophenyl)carboxamido]-1, 1-dimethy1-2-oxobutyl}-3-methyl-4-oxooxetane. The importance of the β-lactone structure for inhibitory activity was found by preparing several derivatives of belactin A.

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The Absolute Configuration of Belactin A, a β-Lactone-Containing Serine Carboxypeptidase Inhibitor: Importance of the β-Lactone Structure for Serine Carboxypeptidase Inhibition

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The Absolute Configuration of Belactin A, a β-Lactone-Containing Serine Carboxypeptidase Inhibitor: Importance of the β-Lactone Structure for Serine Carboxypeptidase Inhibition

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