109114-13-8Relevant articles and documents
ENANTIOSELECTIVE HYDROLYSIS OF ESTERS AND THE OXIDATION OF AROMATIC-ALIPHATIC ALCOHOLS OBTAINED THEREFROM BY SPIRODELA OLIGORRHIZA
Pawlowicz, Pawel,Siewinski, Antoni
, p. 1001 - 1004 (1987)
Spirodela oligorrhiza hydrolyses benzyl acetate and enantiospecifically hydrolyses the acetates of racemic mixtures of 1-phenyl-ethanol, 1-(1-naphthyl)-ethanol, 1-(2-naphthyl)-ethanol, and 2-phenyl-butanol.The R alcohols are formed faster.Two of the resulting alcohols, 1-phenyl-ethanol and 1-(2-naphthyl)-ethanol, undergo an enantiospecific oxidation.Here, the S enantiomers react faster. - Key Word Index: Spirodela oligorrhiza; Lemnaceae; duckweed; biotransformation; benzyl acetate; (+/-)-1-phenyl-ethyl-acetate; (+/-)-1-(1-naphthyl)-ethyl-acetate; (+/-)-1-(2-naphthyl)-ethyl-acetate; (+/-)-2-phenyl-butyl-acetate; acetophenone; 2-acetyl-naphthalene.
A new mechanism of enantioselectivity toward chiral primary alcohol by lipase from Pseudomonas cepacia
Meng, Xiao,Guo, Li,Xu, Gang,Wu, Jian-Ping,Yang, Li-Rong
, p. 109 - 115 (2014/12/11)
The stereo-recognition of chiral primary alcohols by lipase from Pseudomonas cepacia was found to deviate from earlier observations. Enantioselectivity toward 14 pairs of chiral primary alcohol esters by this lipase was dependent on the existence of an Onon-α(oxygen at non-α-position of the acyloxy group) in the alcohol moiety, and decreased as the size of the acyl moiety increased. Chemical modification on the lipase and molecular dynamics simulations indicated that Tyr29located within the catalytic cavity forms a hydrogen bond with the Onon-αof the preferred enantiomer of the primary alcohol ester. However, a larger acyl moiety suffered stronger hindrance from the catalytic cavity wall of the lipase, pushing the Onon-αaway from Tyr29, and thus weakening the stereo-recognition.