Synthesis of 3-(3,4-dihydroxyphenyl)-propionic acid derivatives by N-coupling of amines using laccase

被引：76
作者：
Mikolasch, A [1 ]
Hammer, E [1 ]
Jonas, U [1 ]
Popowski, K [1 ]
Stielow, A [1 ]
Schauer, F [1 ]
机构：
[1] Ernst Moritz Arndt Univ Greifswald, Inst Mikrobiol, D-17489 Greifswald, Germany
来源：
TETRAHEDRON | 2002年 / 58卷 / 38期
关键词：
3-(3,4-dihydroxyphenyl)-propionics; laccase; bio-transformation;
D O I：
10.1016/S0040-4020(02)00872-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Derivatization of the natural compound 3-(3,4-dihydroxyphenyl)-propionic acid (dihydrocaffeic acid) can be achieved by laccase-catalyzed N-coupling of aromatic and aliphatic amines. Incubation of 3-(3,4-dihydroxyphenyl)-propionic acid and 4-aminobenzoic acid with laccase in aqueous medium and in the presence of oxygen yielded 3-[6-(4-carboxyphenyl)amino-3,4-dihydroxyphenyl]-propionic acid as the main product (>80%). Reaction with hexylamine resulted in 3-(6-hexylamino-3,4-dihydroxypheriyl)-propionic acid as the only product (60%). (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：7589 / 7593
页数：5
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