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Falck, J.R. et al.

Falck, Sangras, Capdevila,

Preparation of N-(t)Boc l-glutathione dimethyl and di-tert-butyl esters: Versatile synthetic building blocks.

The title l-glutathione derivatives, containing acid- and base-labile esters, respectively, were obtained in good overall yields. N-(t)Boc l-glutathione dimethyl ester was prepared via Fischer esterification of l-glutathione disulfide (GSSG) using HCl in dry methanol, protection of the amine with (t)Boc(2)O, and tributylphosphine cleavage of the disulfide in wet isopropanol. Alternatively, Fischer esterification and (t)Boc-protection of l-glutathione (GSH) also furnished N-(t)Boc glutathione dimethyl ester accompanied by a small amount of S-(t)Boc that was removed chromatographically. The di-tert-butyl ester was obtained by S-palmitoylation of GSH in TFA as solvent, N-(t)Boc-protection, esterification using (t)BuOH 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.[1]

References

Preparation of N-(t)Boc l-glutathione dimethyl and di-tert-butyl esters: Versatile synthetic building blocks. Falck, J.R., Sangras, B., Capdevila, J.H. Bioorg. Med. Chem. (2007) [Pubmed]

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