Synthesis and Enzymatic Conversion of Amino Acids Equipped with the Silanetriol Functionality: A Prelude to Silicon Biodiversification

Dr. Jade Dussart-Gautheret, Dr. Julie Rivollier, Dr. Cédric Simon, Dr. Alessandro De Simone, Dr. Jérôme Berthet, Prof. Stéphanie Delbaere, Régina Maruchenko, Claire Troufflard, Dr. Denis Lesage, Dr. Yves Gimbert, Dr. Gilles Lemière, Dr. Philippe Marlière, Prof. Louis Fensterbank
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Abstract

Synthetic routes are reported for the three analogues of the simplest L-2-amino-dicarboxylic acids, aspartate, glutamate, and aminoadipate, in which the silanetriol group (Si(OH)3) replaces the distal carboxyl group (CO2H). Direct access to the silanetriol amino acids relied either on catalytic hydrosilylation of a terminal alkene using triethoxysilane, or on alkylation of a glycine equivalent anion by triallyl(iodomethyl)silane. In both cases, acid hydrolysis afforded the silanetriol amino acids. These were shown to self-assemble into siloxane Si-O clusters as their concentration in water increased in the pH range of 1–12. Such reversible cross-linking did not prevent silanetriol amino acids from serving as substrates of an aminotransferase enzyme, boding well for their utilization as microbial nutrients to encompass silicon in future stages of metabolism and polypeptide edifices.

Abstract Image

具有硅三醇功能的氨基酸的合成和酶转化:硅生物多样化的前奏
摘要:本文报道了三种最简单的L - 2 -氨基-二羧酸的类似物——天冬氨酸、谷氨酸和氨基己二酸的合成路线,其中硅三醇基团(Si(OH) 3)取代了远端羧基(CO 2 H)。直接获得硅三醇氨基酸依赖于三乙基氧基硅烷催化的末端烯烃硅氢化反应,或三烯丙基(碘甲基)硅烷催化的甘氨酸等效阴离子烷基化反应。在这两种情况下,酸水解提供了硅三醇氨基酸。结果表明,在pH值为1-12的范围内,当它们在水中的浓度增加时,它们会自组装成硅氧烷Si - O簇。这种可逆交联并没有阻止硅三醇氨基酸作为转氨酶的底物,这预示着它们在未来的代谢和多肽结构中作为微生物营养物质被利用。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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