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pH 依赖的α-氨基酸的化学选择性合成。在水中,由酸稳定的氢化铱配合物催化α-酮酸与氨的还原胺化反应。

pH-Dependent chemoselective synthesis of alpha-amino acids. Reductive amination of alpha-keto acids with ammonia catalyzed by acid-stable iridium hydride complexes in water.

作者信息

Ogo Seiji, Uehara Keiji, Abura Tsutomu, Fukuzumi Shunichi

机构信息

Department of Material and Life Science, Graduate School of Engineering, Osaka University, PRESTO & CREST, Japan Science and Technology Agency (JST), Suita, Osaka 565-0871, Japan.

出版信息

J Am Chem Soc. 2004 Mar 17;126(10):3020-1. doi: 10.1021/ja031633r.

Abstract

An acid-stable hydride complex [CpIrIII(bpy)H]+ {1, Cp = eta5-C5Me5, bpy = 2,2'-bipyridine} serves as the active catalyst for the highly chemoselective synthesis of alpha-amino acids by reductive amination of alpha-keto acids with aqueous NH3 and HCOO- in water at pH 5-8. pH-dependent catalytic 15N- and 2H-double-labeling has also been accomplished by using 15NH3 and DCOONa, which are ideal amine and hydride ion sources, respectively.

摘要

一种酸稳定的氢化物配合物[CpIrIII(bpy)H]+ {1,Cp = η5-C5Me5,bpy = 2,2'-联吡啶}在pH为5 - 8的水中作为活性催化剂,通过α-酮酸与NH3水溶液和HCOO-进行还原胺化反应,实现α-氨基酸的高化学选择性合成。通过使用15NH3和DCOONa分别作为理想的胺和氢负离子源,还完成了pH依赖性催化15N和2H双标记。

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