Enzymatic synthesis of silicon-containing dipeptides with 3-trimethylsilylalanine

被引:7
作者
Ishikawa, H [1 ]
Yamanaka, H [1 ]
Kawamoto, T [1 ]
Tanaka, A [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Synthet Chem & Biol Chem, Lab Appl Biol Chem,Sakyo Ku, Kyoto 6068501, Japan
关键词
D O I
10.1007/s002530051418
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
In this study, the enzymatic synthesis of silicon-containing dipeptides with a silicon-containing amino acid, 3-trimethylsilylalanine (TMS-Ala), was attempted in ethyl acetate, and the effects of TMS-Ala on thermolysin-catalyzed dipeptide synthesis are also discussed. Benzyloxycarbonyl(Z)-TMS-Ala was recognized by thermolysin as a better substrate than Z-Leu, and various silicon-containing dipeptides, Z-(TMS-Ala)-Xaa-OMe (Xaa = Leu, Ile, Phe, etc.), could be obtained. The acceleration of the reaction rate in the synthesis of Z-(TMS-Ala)-Leu-OMe compared with Z-Leu-Leu-OMe synthesis was explained by the higher hydrophobicity of the side-chain of TM S-Ala containing a trimethylsilyl group. On the other hand, TMS-Ala-OMe was not accepted as the amino component because of the bulkiness of the trimethylsilyl group. The enantioselectivity of thermolysin was very high. Z-D-TMS-Ala was not a substrate, while Z-L-TMS-Ala served as a good substrate.
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页码:470 / 473
页数:4
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