Organocatalysis with endogenous compounds: Towards novel non-enzymatic reactions

被引：12

作者：

Alberg, David G. ^{[2
,3
]}

Poulsen, Thomas B. ^{[2
]}

Bertelsen, Soren ^{[2
]}

Christensen, Kasper L. ^{[1
,2
]}

Birkler, Rune D. ^{[1
]}

Johannsen, Mogens ^{[1
]}

Jorgensen, Karl Anker ^{[2
]}

机构：

[1] Aarhus Univ, Sect Toxicol & Drug Anal, Dept Forens Med, DK-8200 Aarhus N, Denmark

[2] Aarhus Univ, Dept Chem, Ctr Catalysis, DK-8000 Aarhus C, Denmark

[3] Carleton Coll, Dept Chem, Northfield, MN 55057 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2009年 / 19卷 / 14期

基金：

新加坡国家研究基金会;

关键词：

Organocatalysis; Aldol; Non-enzymatic; Acetone; Methylglyoxal; SERUM-ALBUMIN; METHYLGLYOXAL; METABOLITE;

D O I：

10.1016/j.bmcl.2009.03.128

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The aldol reaction of the endogeneous compounds acetone and methylglyoxal has been studied using organocatalysis in relation to biologically relevant non-enzymatic reactions. Under preparative conditions, 3-hydroxy-2,5-hexadione, known as Henze's ketol, is formed in high yield and with enantioselectivities up to 88% ee. Furthermore, Henze's ketol is also formed under simulated physiological conditions at micromolar scale, indicating that this reaction might take place in living organisms. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3888 / 3891

页数：4

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