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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen


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Volume 90, Issue 2

Issues

Catalytic processes in the chemistry of lactic acid and PLLA: enzymatic stereoselective alcoholysis of rac-lactide

Ivan A. Shuklov
  • Corresponding author
  • Leibniz-Institut für Katalyse an der Universität Rostock e.V., Albert-Einstein-Str. 29a, 18059 Rostock, Germany
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/ Alexey D. Shuklov / Natalia V. Dubrovina
  • Institut für Chemie der Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
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/ Klaus Kühlein / Armin Börner
  • Corresponding author
  • Leibniz-Institut für Katalyse an der Universität Rostock e.V., Albert-Einstein-Str. 29a, 18059 Rostock, Germany
  • Institut für Chemie der Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
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Published Online: 2017-10-13 | DOI: https://doi.org/10.1515/pac-2017-0412

Abstract

The preparation of the enantiomerically pure (R,R)-lactide (>99%ee) on the gram scale by alcoholysis of rac-lactide in the presence of Amano lipase PS is described. The synthesis of enantiopure lactide by this method is advantageous over traditional preparation via thermal tin-catalysed cyclisation of corresponding oligolactic acids, since the reaction temperature are much lower. That results that no meso-lactide is formed. The alcoholysis of rac-lactide with n-BuOH was studied in the presence of various enzymes in different solvent systems. The kinetic study of the alcoholysis of rac-lactide in the presence of CALB was performed.

Keywords: asymmetric synthesis; enzyme catalysis; ICGC-6; kinetic resolution; lactic acid; lactides

Article note:

A collection of invited papers based on presentations at the 6th international IUPAC Conference on Green Chemistry (ICGC-6), Venice (Italy), 4–8 September 2016.

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About the article

Published Online: 2017-10-13

Published in Print: 2018-02-23


Citation Information: Pure and Applied Chemistry, Volume 90, Issue 2, Pages 285–292, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1515/pac-2017-0412.

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