Scalable Lipase-Catalyzed Synthesis of (R)-4-(Acyloxy)pentanoic Acids from Racemic γ-Valerolactone

Parve, Jaan, Kudryašova, Marina, Shalima, Tatsiana , Villo, Ly, Liblikas, Ilme, Reile, Indrek, Pehk, Tõnis, Gathergood, Nicholas, Aav, Riina, Vares, Lauri and Parve, Omar (2021) Scalable Lipase-Catalyzed Synthesis of (R)-4-(Acyloxy)pentanoic Acids from Racemic γ-Valerolactone. ACS Sustainable Chemistry & Engineering, 9 (4). pp. 1494-1499. ISSN 2168-0485

Full content URL: https://doi.org/10.1021/acssuschemeng.0c07918

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Scalable Lipase-Catalyzed Synthesis of (R)-4-(Acyloxy)pentanoic Acids from Racemic γ-Valerolactone
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Abstract

Conversion of biobased platform chemicals to enantiopure compounds has become topical. We report a straightforward synthesis of 4-(acyloxy)-pentanoic acids from gamma-valerolactone (GVL). An alkaline hydrolysis of GVL is followed by a stereoselective lipase-catalyzed acylation of the sodium salt. Acidic hydrolysis of the acylation product affords (R)-4-(acyloxy)-pentanoic acid and relactonized (S)-GVL. (R)-4-(Propionyloxy)-pentanoic acid and (R)-GVL are obtained with e.r. > 99/1. An additional enzymatic step following a slightly modified process affords (S)-4-(acetyloxy)pentanoic acid with e.r. > 99/1. Simple access to enantiopure 4-(acyloxy)pentanoic acids will stimulate the development of their novel applications, including biobased isotactic polymers.

Keywords:enzyme catalysis, green chemistry, biopolymers
Subjects:F Physical Sciences > F100 Chemistry
F Physical Sciences > F163 Bio-organic Chemistry
Divisions:College of Science > School of Chemistry
ID Code:46489
Deposited On:15 Sep 2021 13:21

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