Enantiopreference of Lipase from Pseudomonas cepacia toward Primary Alcohols

Molecular basis of lipase stereoselectivity

“…Weissfloch and Kazlauskas [27] proposed a similar rule to predict the stereopreference of PCL toward primary alcohols (Fig. 1b).…”

“…lipases from Pseudomonas cepacia (PCL) [26,27], Pseudomonas aeruginosa [28], P. fluorescens [29], Candida rugosa (CRL) [26,[30][31][32], RML [33], and porcine pancreatic lipase [34,35]. Although the degree of stereoselectivity varies for different alcohols and enzymes, all lipases and esterases tested preferred the enantiomer shown (Fig.…”

“…1. Empirical rule that summarizes the enantiopreference of Pseudomonas cepacia lipase toward chiral alcohols [26,27]. a) The favored enantiomer for secondary alcohols, b) the favored enantiomer for primary alcohols.…”

Chemoenzymatic Synthesis of (+)-.ALPHA.-Polypodatetraene and Methyl (5R,10R,13R)-Labda-8-en-15-oate

“…The empirical rule summarize the enantioperference of PCL toward primary alcohol or its acylated derivative as shown in Chart 5. 14,15) When the hydroxy methyl (-CH 2 OH) or acyloxy methyl (-CH 2 OCOR) groups exist back with the plane of the page, the favored enantiomer bears a large substituent (L) on the right, and a medium substituent (M) on the left. In the present case, prediction of enantioperference toward primary alcohol (Ϯ)-17 was fairly explained by the empirical rule.…”

Enzymatic Resolution of (.+-.)-5-Acetoxy-4-aryl-(2E)-pentenoate Derivatives

“…1. 17,18) When the hydroxyl methyl (-CH 2 OH) or acyloxy methyl (-CH 2 OCOR) group exists in the plane of the page, the favored enantiomer bears a large substituent (L) on the right, and a medium substituent (M) on the left. The enantiopreference toward primary alcohols or their acetates using lipase OF-360 from Candida rugosa might be explained by the present empirical rule.…”