Synthesis of 1,2-Di-O-acyl-3-thioglycerols for Lipid Modification of Peptides and Proteins

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Abstract
Thiol-functionalized lipids were synthesized to exploit thiol-specific reaction principles for the selective conjugation of lipid moieties to peptides and proteins. Thioglycerol (3-mercapto-1,2-propanediol) protected as S-tert-butylthio derivative served as starting product for the esterification of the two hydroxy groups with identical saturated or unsaturated fatty acids as well as for the preparation of mixed diacyl derivatives. Reductive cleavage of the thiol protecting group produced the (RS)-1,2-di-O-acyl-3-thioglycerols (RS)- 2,3-diacyloxypropanethiols as suitable reagents for lipid modification of target molecules.

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