Preparation of N-tBoc L-glutathione dimethyl and di-tert-butyl esters: versatile synthetic building blocks.

Preparation of N-tBoc L-glutathione dimethyl and di-tert-butyl esters: versatile synthetic building blocks. Research Abstract Details 

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Preparation of N-tBoc L-glutathione dimethyl and di-tert-butyl esters: versatile synthetic building blocks. Abstract Text:

J R Falck,Bhavani Sangras,Jorge H Capdevila,

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.

Preparation of N-tBoc L-glutathione dimethyl and di-tert-butyl esters: versatile synthetic building blocks. Publishing Authors By Initials

JR Falck,B Sangras,JH Capdevila,

For similar chemical actions and uses: specialty uses of chemicals: solvents research abstracts see: chemical actions and uses: specialty uses of chemicals: solvents research

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Preparation of N-tBoc L-glutathione dimethyl and di-tert-butyl esters: versatile synthetic building blocks. Journal Published:

PUBLICATION TYPE: Research Support, N.I.H., Extr

Journal: Bioorganic & medicinal chemistry

VOLUME: 15

Page Numbers: 1062-6

Journal Abbreviation: Bioorg. Med. Chem.

ISSN: 0968-0896

DAY: 25

MONTH: 10

YEAR: 2006

Preparation of N-tBoc L-glutathione dimethyl and di-tert-butyl esters: versatile synthetic building blocks. Information

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LANGUAGE: eng

NlmUniqueID: 9413298

Preparation of N-tBoc L-glutathione dimethyl and di-tert-butyl esters: versatile synthetic building blocks. Keywords Mesh Terms:

KEYWORDS: Solvents

MESH TERMS: chemistry

Chemical & Substance for Abstract: Preparation of N-tBoc L-glutathione dimethyl and di-tert-butyl esters: versatile synthetic building blocks. Information

Substance Name: Glutathione

Registry Number: 70-18-8

Grant and Affiliation Information for Preparation of N-tBoc L-glutathione dimethyl and di-tert-butyl esters: versatile synthetic building blocks.

AFFILIATION: Departments of Biochemistry and Pharmacology, University of Texas Southwestern Medical Center, Dallas, TX 75390-9038, USA. j.falck@UTSouthwestern.edu

Country: England

AGENCY: United States NIGMS

GRANT: R01 GM037922-16

ACRONYM: GM

MEDLINETA: Bioorg Med Chem

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