Premium
Lipolytic synthesis of optically active 1,2‐dibutyryl‐ sn ‐glycerol. Identification of diglyceride by solvent‐dependent specific rotation
Author(s) -
O’Connor Charmian J.,
Lai Douglas T.,
Barton Richard H.
Publication year - 1998
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-998-0288-0
Subject(s) - chemistry , diglyceride , hydrolysis , glycerol , lipase , yield (engineering) , diacylglycerol kinase , solvent , specific rotation , enzyme , biochemistry , organic chemistry , materials science , protein kinase c , metallurgy
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 13 C 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, CHCl 3 ) and +3.32° (c ∼1.2, pyridine), and confirmation of sn ‐3 specificity by pregastric lipase was obtained.