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Hydrolytic enzymes in the synthesis of carba-sugars: application of the lipase from Pseudomonas fragi

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UNSPECIFIED (1998) Hydrolytic enzymes in the synthesis of carba-sugars: application of the lipase from Pseudomonas fragi. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 (6). pp. 1065-1068.

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Abstract

Pig liver esterase-catalysed hydrolysis of (+/-)-endo-2-methoxycarbonyl-7-oxabicyclo[2.2.1]hept-5-ene 1a provides (-)-endo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid 1b and (+)-endo-2-methoxycarbonyl-7-oxabicyclo[2.2.1]hept-5-ene 1a in 36 and 57% ee, respectively. Transesterification between (+/-)-2-exo-hydroxy-4,8-dioxatricyclo[4.2.1.0(3,7)]nonan-5-one 2a and vinyl acetate catalysed by the lipase from Pseudomonas fragi gives the acetate (-)-2b and alcohol (+)-2a in 91 and 94% ee, respectively, Optically pure acetate (-)-2b is obtained after removal of contaminating racemate from the impure acetate by crystallisation of(-)-2b of 91% ee (EtOH).

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Journal or Publication Title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Publisher: ROYAL SOC CHEMISTRY
ISSN: 0300-922X
Official Date: 21 March 1998
Dates:
DateEvent
21 March 1998UNSPECIFIED
Number: 6
Number of Pages: 4
Page Range: pp. 1065-1068
Publication Status: Published

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