title: Bioresolution of (R)-glycidyl azide by Aspergillus niger ZJUTZQ208: a new and concise synthon for chiral vicinal amino alcohols.
abstract: A newly isolated Aspergillus niger strain containing epoxide hydrolase was used to resolve racemic glycidyl azide and four derivatives to the (R)-enantiomers. After optimization of the biotransformation conditions, (R)-glycidyl azide was produced with good enantioselectivity (e.e.s > 95 %, E > 20). The substrate structure, pH, and reaction time were found to have profound influences on the catalytic property of A. niger ZJUTZQ208. Enantiopure glycidyl azide was further utilized to synthesize linezolid in good yield, indicating it is a new and concise synthon for chiral vicinal amino alcohols. Enzyme-substrate docking studies were carried out with glycidyl azide to study the selectivity of this strain.
authors.affiliation: Institute of Bioengineering, Zhejiang University of Technology, Chaowang Road 18, Hangzhou 310014, China.
authors.forename: Lin
authors.initials: L
authors.lastname: Chen
authors.forename: Honglei
authors.initials: H
authors.lastname: Shen
authors.forename: Chun
authors.initials: C
authors.lastname: Wei
authors.forename: Qing
authors.initials: Q
authors.lastname: Zhu
mesh_terms: D000081:Acetamides / Q000378:metabolism; D000605:Amino Alcohols / Q000378:metabolism*; D000900:Anti-Bacterial Agents / Q000378:metabolism; D001234:Aspergillus niger / Q000145:classification / Q000201:enzymology / Q000302:isolation & purification / Q000378:metabolism*; D001711:Biotransformation; D016000:Cluster Analysis; D004271:DNA, Fungal / Q000737:chemistry / Q000235:genetics; D004275:DNA, Ribosomal / Q000737:chemistry / Q000235:genetics; D004851:Epoxide Hydrolases / Q000737:chemistry / Q000378:metabolism; D020459:Genes, rRNA; D006863:Hydrogen-Ion Concentration; D000069349:Linezolid; D008958:Models, Molecular; D056004:Molecular Dynamics Simulation; D008969:Molecular Sequence Data; D023303:Oxazolidinones / Q000378:metabolism; D010802:Phylogeny; D011108:Polymers / Q000378:metabolism*; D012331:RNA, Fungal / Q000235:genetics; D012337:RNA, Ribosomal, 18S / Q000235:genetics; D017422:Sequence Analysis, DNA; D013997:Time Factors
chemical_list: D000081:Acetamides; D000605:Amino Alcohols; D000900:Anti-Bacterial Agents; D004271:DNA, Fungal; D004275:DNA, Ribosomal; D023303:Oxazolidinones; D011108:Polymers; D012331:RNA, Fungal; D012337:RNA, Ribosomal, 18S; C530353:glycidyl azide polymer; D004851:Epoxide Hydrolases; D000069349:Linezolid