Influence of organic solvents on enzyme chemoselectivity and their role in enzyme-substrate interaction

被引：11

作者：

Ebert, C ^{[1
]}

Gardossi, L ^{[1
]}

Linda, P ^{[1
]}

Vesnaver, R ^{[1
]}

Bosco, M ^{[1
]}

机构：

[1] POLY BIOS LBT,I-34012 TRIESTE,ITALY

来源：

TETRAHEDRON | 1996年 / 52卷 / 13期

关键词：

D O I：

10.1016/0040-4020(96)00158-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chemoselectivity of lipoprotein lipase from Pseudomonas specie is strongly influenced by solvation phenomena and can be modulated by changing the reaction medium. Experimental results obtained from enzymatic acylation of L-Ser-beta-naphthylamide indicated that chemoselectivity depends on the nature of hydrogen bonds taking place among the molecular species present in the reaction medium, Inverted selectivity was observed upon moving from hydrogen bond donor solvents to hydrogen bond acceptor solvents. Solvent hgdrophobicity can also influence chemoselectivity inducing intramolecular electrostatic interactions which alter the reactivity of the nucleophilic group(s). Solvation phenomena were studied by means of H-1 NMR. An explanation of interactions between the solvated substrate and the enzyme is also proposed.

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收藏

页码：4867 / 4876

页数：10

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