Study on Surfactin, a Cyclic Depsipeptide. II. Synthesis of Surfactin B_2 Produced by Bacillus natto KMD 2311

概要

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The total synthesis of surfactin B_2,a cyclic depsipeptide isolated from Bacillus natto KMD 2311,was achieved to elucidate the absolute configuration of its fatty acid moiety. This is the first chemical confirmation of the absolute configuration of a surfactin homolog. Two possible diastereoisomers of surfactin B_2,cyclo[D- and L-3-(Glu-Leu-D-Leu-Val-Asp-D-Leu-Leu-O)-n-tetradecanoyl] (1a and b), were synthesized by a solution method using mainly active ester and azide fragment condensation methods. Cyclization reaction of the partially protected linear depsipeptide containing the C-terminal N-succinimidyl active ester in pyridine by the high dilution method at room temperature for 3d gave the desired cyclic depsipeptide in a high yield of about 70%. The synthetic product 1a, containing the D-isomer of 3-hydroxytetradecanoic acid as a fatty acid moiety, was identical with natural surfactin B_2.
社団法人日本薬学会の論文
1996-01-15