Biocatalytic Approaches towards the Synthesis of Chiral Amino Alcohols from Lysine: Cascade Reactions Combining alpha-Keto Acid Oxygenase Hydroxylation with Pyridoxal Phosphate- Dependent Decarboxylation

被引：24

作者：

Baud, Damien ^{[1
,2
,3
,4
]}

Peruch, Olivier ^{[1
,2
,3
]}

Saaidi, Pierre-Loic ^{[1
,2
,3
]}

Fossey, Aurelie ^{[1
,2
,3
]}

Mariage, Aline ^{[1
,2
,3
]}

Petit, Jean-Louis ^{[1
,2
,3
]}

Salanoubat, Marcel ^{[1
,2
,3
]}

Vergne-Vaxelaire, Carine ^{[1
,2
,3
]}

de Berardinis, Veronique ^{[1
,2
,3
]}

Zaparucha, Anne ^{[1
,2
,3
]}

机构：

[1] CEA, DRF, IG, Genoscope, 2 Rue Gaston Cremieux, F-91057 Evry, France

[2] CNRS, Genom & Metabol UMR8030, 2 Rue Gaston Cremieux, F-91057 Evry, France

[3] Univ Evry Val dEssonne, Blvd Francois Mitterrand, F-91025 Evry, France

[4] UCL, Dept Chem, 20 Gordon St, London WC1H 0AJ, England

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 09期

关键词：

biocatalysis; cascade reactions; chiral amino alcohols; decarboxylases; dioxygenases; SUBSTRATE-SPECIFICITY; ASYMMETRIC-SYNTHESIS; 1,2-AMINO ALCOHOLS; IDENTIFICATION; DERIVATIVES; REDUCTION; DIAMINE; SYSTEM; COLI;

D O I：

10.1002/adsc.201600934

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Amino alcohols are a very common structural motif in natural and synthetic molecules. Starting from l-lysine and hydroxy-l-lysine, a straightforward biocatalytic synthesis of beta- and gamma-amino alcohols is presented. Diastereoselective C-H oxidation catalyzed by an alpha-keto acid-dependent oxygenase followed by cleavage of the carboxylic acid moiety of the corresponding chiral hydroxy amino acid by a pyridoxal phosphate-dependent decarboxylase enabled the formation of the target amino alcohols with moderate to complete conversions. Four beta- and gamma-amino alcohols were obtained on a small scale in excellent yields and stereoselectivities.

引用

页码：1563 / 1569

页数：7

共 33 条

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