Chemoenzymatic synthesis of optically active α-methylene-γ-carboxy-γ-lactams and γ-lactones

被引：14
|
作者：
Bertoli, Annalisa [1 ]
Fanfoni, Lidia [1 ]
Felluga, Fulvia [1 ]
Pitacco, Giuliana [1 ]
Valentin, Ennio [1 ]
机构：
[1] Univ Trieste, Dipartimento Sci Chim, I-34127 Trieste, Italy
来源：
TETRAHEDRON-ASYMMETRY | 2009年 / 20卷 / 19期
关键词：
INDIUM-PROMOTED PREPARATION; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; 4-METHYLENE-L-GLUTAMIC ACID; STEREOCONTROLLED SYNTHESIS; SESQUITERPENE LACTONES; TUMOR INHIBITORS; AMINO-ACIDS; REAGENTS; ALDEHYDES;
D O I：
10.1016/j.tetasy.2009.09.009
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Three alpha-methylene-gamma-carbomethoxy-gamma-butyrolactams (methyl alpha-methylene-pyroglutamates) 11, 12 and 13, differing in the substitution at the heterocyclic nitrogen, as well as the structurally related gamma-lactones 14 and 15 were synthesised and resolved enzymatically by hydrolysis of their ester function, mediated by commercially available hydrolytic enzymes. In particular, the alpha-chymotrypsin proved to be active to all the substrates examined, displaying a different degree of activity and enantioselectivity, this latter increasing significantly towards the substrate with an aromatic substituent at the nitrogen. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2305 / 2310
页数：6
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