Preparation of N-tBoc l-glutathione dimethyl and di-tert-butyl esters: Versatile synthetic building blocks

J R Falck, Bhavani Sangras, Jorge H. Capdevila

Research output: Contribution to journalArticle

22 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)1062-1066
Number of pages5
JournalBioorganic and Medicinal Chemistry
Volume15
Issue number2
DOIs
StatePublished - Jan 15 2007

Fingerprint

Glutathione
Esters
Esterification
Glutathione Disulfide
Lipoylation
Saponification
Derivatives
2-Propanol
Disulfides
Amines
Methanol
Acids

Keywords

  • Amino acids and derivatives
  • Peptides
  • Protecting groups
  • Thioesters

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Preparation of N-tBoc l-glutathione dimethyl and di-tert-butyl esters : Versatile synthetic building blocks. / Falck, J R; Sangras, Bhavani; Capdevila, Jorge H.

In: Bioorganic and Medicinal Chemistry, Vol. 15, No. 2, 15.01.2007, p. 1062-1066.

Research output: Contribution to journalArticle

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