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Abstract
Oxidized l-glutathione was esterified to the tetra methyl ester using thionyl chloride in methanol solvent. Other alcohols were tested and the reaction progress was monitored via ESI-MS. This procedure proved to be compatible with other small peptides not containing serine and cysteine residues. In contrast to previously reported methods this procedure provided convenient access to esterified peptides requiring no purification, extended reaction times, or complicated reaction setups.
Highlights
The design and synthesis of novel glutathione analogues are studied extensively for their pharmacological properties in the treatment of a wide range of diseases [1,2,3]
In our hands the reported Fischer esterification protocol required extensive purification and the isolated yield was too low to be of practical value
We extended the method to other peptides in order to gain an understanding of the compatibility with other protogenic amino acids
Summary
The design and synthesis of novel glutathione analogues are studied extensively for their pharmacological properties in the treatment of a wide range of diseases [1,2,3]. One approach to synthesize protected GSH analogues is to start with the readily available disulfide dimmer of GSH, L-glutathione (GSSG) 1. GSSG is affordable and the sulfhydryl functional groups are protected in their disulfide form. Additional esterification strategies include utilizing trimethylsilyl chloride in methanol solvent [2,8] and the use of diazomethane to form methyl esters [9,10]. We report a convenient synthesis of 2a using thionyl chloride in methanol solvent as illustrated in Scheme 1. This method eliminated side reactions, long reaction times, and column purification. Preparation of oxidized glutathione tetra-alkyl esters (GSSG(OR)4) from oxidized glutathione (GSSG) using thionyl chloride in alcohol solvent
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