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Preparation of optically active D ‐arylglycines for use as side chains for semisynthetic penicillins and cephalosporins using immobilized subtilisins in two‐phase systems
Author(s) -
Schutt Hermann,
SchmidtKastner Günter,
Arens Alfred,
Preiss Michael
Publication year - 1985
Publication title -
biotechnology and bioengineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.136
H-Index - 189
eISSN - 1097-0290
pISSN - 0006-3592
DOI - 10.1002/bit.260270406
Subject(s) - chemistry , hydrolysis , substituent , subtilisin , yield (engineering) , organic chemistry , solubility , substrate (aquarium) , bioconversion , side chain , enzymatic hydrolysis , chromatography , enzyme , combinatorial chemistry , stereochemistry , polymer , materials science , oceanography , metallurgy , geology , fermentation
Optically active D ‐arylglycines, which are of interest for preparation of semisynthetic penicillins and cephalosporins, were isolated from the racemic mixtures of their derivatives using immobilized proteolytic enzyme subtilisin (EC No. 3.4.4. 16). The performance of these reactions in two‐phase systems, consisting of water and an immiscible organic solvent, improved the yield, purity, and economics of the process by increasing the substrate solubility and reducing the rate of nonenzymatic hydrolysis. The proportion of the organic phase can be as much as 75% of the overall volume without seriously impairing the enzymatic activity. The optically pure D ‐and L ‐arylglycines were liberated from their D ‐ and L ‐derivatives by acid hydrolysis. The substituent influence of the various arylglycine derivatives on the rate of the enzymatic cleavage reaction was investigated.