Improved Large-Scale Synthesis of(<i>R</i>)-Benzyl 4-Hydroxyl-2-pentynoate from (<i>R</i>)-3-Butyn-2-ol

A triple mutant of an esterase from Pseudomonas fluorescens (PFE) that was created by directed evolution exhibited high enantioselectivity (E=89) in a kinetic resolution and yielded the building block (S)-but-3-yn-2-ol. Surprisingly, a mutation close to the active site caused the formation of inclusion bodies, but remote mutations were found to be responsible for the high selectivity. Back mutations gave a variant (double mutant PFE Ile76Val/Val175Ala) that showed excellent selectivity (E=96) and activity (20 min for 50% conversion, which corresponds to 1.25 U per mg of protein).

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Highly enantioselective reduction of 4-(trimethylsilyl)-3-butyn-2-one to enantiopure (R)-4-(trimethylsilyl)-3-butyn-2-ol using a novel strain Acetobacter sp. CCTCC M209061

Xiao

Zong

Lou

2009

Bioresource Technology

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Improved Large-Scale Synthesis of(R)-Benzyl 4-Hydroxyl-2-pentynoate from (R)-3-Butyn-2-ol

Cited by 6 publications

References 3 publications

Surveying Enantioselectivity of Two Candida antarctica‐lipase‐B Homologs Towards Chiral sec‐Alcohols

Surveying Enantioselectivity of Two Candida antarctica‐lipase‐B Homologs Towards Chiral sec‐Alcohols

Directed Evolution of an Esterase from Pseudomonas fluorescens Yields a Mutant with Excellent Enantioselectivity and Activity for the Kinetic Resolution of a Chiral Building Block

Highly enantioselective reduction of 4-(trimethylsilyl)-3-butyn-2-one to enantiopure (R)-4-(trimethylsilyl)-3-butyn-2-ol using a novel strain Acetobacter sp. CCTCC M209061

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