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Facile Synthesis of S ‐Substituted L‐Cysteines with Nano‐sized Immobilized O ‐Acetylserine Sulfhydrylase
Author(s) -
Vahidi Akbar K.,
Wang Zunsheng,
Li Zhi
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201800577
Subject(s) - nitrilotriacetic acid , chemistry , yield (engineering) , cysteine , enzyme , biotransformation , immobilized enzyme , artificial enzyme , biocatalysis , combinatorial chemistry , aryl , organic chemistry , catalysis , chelation , reaction mechanism , materials science , alkyl , metallurgy
Many S ‐substituted l ‐cysteines are useful pharmaceutical intermediates but require a simple synthesis method. Here we developed enzymatic synthesis of several S ‐aryl‐ l ‐cysteines and S ‐benzyl‐ l ‐cysteine directly from O ‐acetylserine (OAS) with immobilized O ‐acetylserine sulfhydrylase CysM. Novel iron‐oxide magnetic nanoparticles (MNPs) with cobalt‐nitrilotriacetic acid function were prepared with a diameter of 80 nm in 75 % yield. Direct immobilization of His‐tagged CysM in the cell‐free extract on the MNPs via affinity attachment afforded stable nanobiocatalyst with 97 % enzyme loading efficiency and 93 % free enzyme activity. The immobilized enzyme catalyzed the biotransformation of benzylthiol and OAS to give S ‐benzyl‐ l ‐cysteine in 88 % yield. The nanobiocatalyst also demonstrated high recyclability, retaining 95 % productivity in the fifth cycle. The immobilized CysM accepts various arylthiols to react with OAS, giving rise to a new synthesis route of several S ‐substituted l ‐cysteines in 60–96 % yield.