Stereoselective Synthesis of β-Methoxytyrosine Derivatives for Identification of the Absolute Configuration of Callipeltin E

Hiroyuki Konno; Sachiyo Aoyama; Kazuto Nosaka; Kenichi Akaji

doi:10.1055/s-2007-990848

PAPER

Stereoselective Synthesis of β-Methoxytyrosine Derivatives for Identification of the Absolute Configuration of Callipeltin E

Hiroyuki Konno*^a, Sachiyo Aoyama^b, Kazuto Nosaka^a, Kenichi Akaji^a
^a Department of Chemistry, Graduate School of Medical Sciences, Kyoto Prefectural University of Medicine, Kita-ku, Kyoto 603-8334, Japan
Fax: +81(75)4657659; e-Mail: konno@koto.kpu-m.ac.jp;
^b Department of Biological Science and Technology, Faculty of Engineering, University of Tokushima, 2-1 Minamijosanjima-cho, Tokushima 770-8506, Japan

Abstract

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Abstract

Asymmetric syntheses of all diastereoisomers of β-methoxytyrosine, an unusual amino acid contained in callipeltin A, were accomplished starting from a cinnamyl ester derivative. The stereochemistry of β-methoxytyrosine in callipeltin E was estimated to be 2R,3R by ¹H and ¹³C NMR analyses of four diastereoisomeric tripeptides, each containing a β-methoxytyrosine isomer. These results obtained from the synthetic peptide derivatives were identical to D’Auria’s results obtained by a degradative procedure.

Key words

callipeltin - cyclodepsipeptide - β-methoxytyrosine - marine sponge - unusual amino acid - anti-HIV activity

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