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Lipolytic synthesis of optically active 1,2-dibutyryl-sn-glycerol. Identification of diglyceride by solvent-dependent specific rotation

Authors
  • O’Connor, Charmian J.
  • Lai, Douglas T.
  • Barton, Richard H.
Type
Published Article
Journal
Journal of the American Oil Chemists’ Society
Publisher
Springer-Verlag
Publication Date
Aug 01, 1998
Volume
75
Issue
8
Pages
1061–1062
Identifiers
DOI: 10.1007/s11746-998-0288-0
Source
Springer Nature
Keywords
License
Yellow

Abstract

The objective was to determine whether the initial pregastric lipase catalyzed hydrolysis of a triacylglycerol to 1,2(2,3)-diacylglycerol was a consequence of sn-specific hydrolysis. The identity of the reaction products for the enzyme-assisted hydrolysis and uncatalyzed acyl-transfer reaction sequence of tributyrylglycerol was assigned by 13C nuclear magnetic resonance. The optical activity of the product 1,2-dibutyryl-sn-glycerol (yield >50%, pH 6.5, 35°C, 13 min) was solvent dependent, being −2.92° (c ∼1.3, CHCl3) and +3.32° (c ∼1.2, pyridine), and confirmation of sn-3 specificity by pregastric lipase was obtained.

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