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Biocatalytic synthesis of ascorbyl esters and their biotechnological applications

Abstract

Ascorbyl fatty acid esters act both as antioxidants and surfactants. These esters are obtained by acylation of vitamin C using different acyl donors in presence of chemical catalysts or lipases. Lipases have been used for this reaction as they show high regioselectivity and can be used under mild reaction conditions. Insolubility of hydrophilic ascorbic acid in non-polar solvents is the major obstacle during ascorbic acid esters synthesis. Different strategies have been invoked to address this problem viz. use of polar organic solvents, ionic liquids, and solid-phase condensation. Furthermore, to improve the yield of ascorbyl fatty acid esters, reactions were performed by (1) controlling water content in the reaction medium, (2) using vacuum to remove formed volatile side product, and (3) employing activated acyl donors (methyl, ethyl or vinyl esters of fatty acids). This mini-review offers a brief overview on lipase-catalyzed syntheses of vitamin C esters and their biotechnological applications. Also, wherever possible, technical viability, scope, and limitations of different methods are discussed.

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Acknowledgement

The author is grateful to Prof. Anju Chadha (IIT Madras, India), Prof. Walter Leitner (ITMC, RWTH Aachen University, Germany) and Dr Lasse Greiner (ITMC, RWTH Aachen University, Germany) for fruitful discussions.

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Correspondence to Sanjib Kumar Karmee.

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Karmee, S.K. Biocatalytic synthesis of ascorbyl esters and their biotechnological applications. Appl Microbiol Biotechnol 81, 1013–1022 (2009). https://doi.org/10.1007/s00253-008-1781-y

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Keywords

  • Vitamin C ester
  • Esterification
  • Transesterification
  • Lipase
  • Antioxidant