Abstract
The title l-glutathione derivatives, containing acid- and base-labile esters, respectively, were obtained in good overall yields. N-tBoc l-glutathione dimethyl ester was prepared via Fischer esterification of l-glutathione disulfide (GSSG) using HCl in dry methanol, protection of the amine with tBoc2O, and tributylphosphine cleavage of the disulfide in wet isopropanol. Alternatively, Fischer esterification and tBoc-protection of l-glutathione (GSH) also furnished N-tBoc glutathione dimethyl ester accompanied by a small amount of S-tBoc that was removed chromatographically. The di-tert-butyl ester was obtained by S-palmitoylation of GSH in TFA as solvent, N-tBoc-protection, esterification using tBuOH mediated by diisopropylcarbodiimide/copper(I) chloride, and saponification of the thioester. These l-glutathione derivatives are versatile synthetic building blocks for the preparation of S-glutathione adducts.
Original language | English (US) |
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Pages (from-to) | 1062-1066 |
Number of pages | 5 |
Journal | Bioorganic and Medicinal Chemistry |
Volume | 15 |
Issue number | 2 |
DOIs | |
State | Published - Jan 15 2007 |
Keywords
- Amino acids and derivatives
- Peptides
- Protecting groups
- Thioesters
ASJC Scopus subject areas
- Biochemistry
- Molecular Medicine
- Molecular Biology
- Pharmaceutical Science
- Drug Discovery
- Clinical Biochemistry
- Organic Chemistry