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Thiol esters of 2-mercaptoethanol and 3-mercapto-1,2-propanediol

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Lipids

Abstract

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.

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Abbreviations

DCC:

dicyclohexylcarbodiimide

DMAP:

dimethyl-aminopyridine

GC-MS:

gas chromatography-mass spectra

GLC:

gas liquid chromatography

HMPT:

hexamethylphosphoric triamide

i.d.:

inner diameter

IR:

infrared spectra

TLC:

thin-layer chromatography

UV:

ultraviolet

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Authors and Affiliations

  1. ARS, Eastern Regional Research Center, U.S. Department of Agriculture, 600 East Mermaid Lane, 19118, Philadelphia, PA

    Philip E. Sonnet

  2. Pennsylvania State University, Ogontz Campus, Abington, PA

    Gordon G. Moore

Authors
  1. Philip E. Sonnet
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  2. Gordon G. Moore
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Sonnet, P.E., Moore, G.G. Thiol esters of 2-mercaptoethanol and 3-mercapto-1,2-propanediol. Lipids 24, 743–745 (1989). https://doi.org/10.1007/BF02535215

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  • DOI: https://doi.org/10.1007/BF02535215

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