Premium
Thiol esters of 2‐mercaptoethanol and 3‐mercapto‐1,2‐propanediol
Author(s) -
Sonnet Philip E.,
Moore Gordon G.
Publication year - 1989
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02535215
Subject(s) - thiol , chemistry , lipase , reagent , fatty acid , propanediol , catalysis , organic chemistry , enzyme
2‐Mercaptoethanol and 3‐mercapto‐1,2‐propanediol are selectively S‐acylated by fatty acids with dicyclohexylcarbodiimide (DCC) catalyzed by 4‐dimethylaminopyridine. Since reaction of such thiols with acid halides produces mixtures of S‐ and O‐acylated materials, the procedure using DCC is more efficient. Such thiol esters are valuable as substrates in the study of lipase activity, using Ellman's Reagent in a continuous spectrophotometric assay. This selective synthesis will facilitate the study of fatty acid residues that are less available. Rearrangement of S‐ to O‐acylated compounds occurs only slowly under the conditions of the lipase assay and should not significantly affect activity measurements. Using DCC, it is possible to sequentially esterify 2‐mercaptoethanol to form unsymmetrical diesters.