Enzymatic procedures in the preparation of regioprotected D-fructose derivatives.

Carbohydr Res

CNR Istituto Chimica Biomolecolare, Sezione CT, via del santuario 110, 95028 Valverde CT, Italy.

Published: February 2005

AI Article Synopsis

  • A mix of lipases from various sources like Pseudomonas cepacia and Candida species facilitated the regioesterification of free fructose to create several acetylated fructofuranose compounds.
  • Utilizing lipases from C. antarctica B and C. rugosa, the alcoholysis of fructose peracetate yielded both tetra-O-acetyl forms of alpha and beta-D-fructofuranose.
  • One specific product, 1,4,6-tri-O-acetyl-D-fructofuranose, was effectively used to synthesize the rare ketohexose D-psicose.

Article Abstract

A combination of different lipases from Pseudomonas cepacia, Candida antarctica B, Candida rugosa and Mucor miehei, aided the regioesterification of the free fructose allowing the synthesis of 1,6-di-O-acetyl-D-fructofuranose, 1,4,6-tri-O-acetyl-D-fructofuranose, 1,6-di-O-acetyl-4-O-benzoyl-D-fructofuranose and 1,6-di-O-benzoyl-D-fructofuranose. Using C. antarctica B and C. rugosa lipases the alcoholysis of fructose peracetate (alpha, beta-form) has furnished 1,2,3,4-tetra-O-acetyl-alpha-D-fructofuranose and 2,3,4,6-tetra-O-acetyl-beta-D-fructofuranose. 1,4,6-Tri-O-acetyl-D-fructofuranose was successfully employed to produce a rare ketohexose, namely D-psicose.

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http://dx.doi.org/10.1016/j.carres.2004.11.003DOI Listing

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