120033-58-1

Basic information

• Product Name: N-tert-Butyloxycarbonyl Glutathione DiMethyl Diester
• Synonyms: N-tert-Butyloxycarbonyl Glutathione DiMethyl Diester;N-[(1,1-DiMethylethoxy)carbonyl]-L-γ-glutaMyl-L-cysteinyl-glycine DiMethyl Ester;N-[N-[N-[(1,1-diMethylethoxy)carbonyl]-L-γ-glutaMyl]-L-cysteinyl]-glycine DiMethyl Ester
• CAS NO: 120033-58-1
• Molecular Formula: C₁₇H₂₉N₃O₈S
• Molecular Weight: 435.49246
• Product Categories: Amino Acids & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;Amino Acids & Derivatives, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 120033-58-1.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: N-tert-Butyloxycarbonyl Glutathione DiMethyl Diester(CAS DataBase Reference)
• NIST Chemistry Reference: N-tert-Butyloxycarbonyl Glutathione DiMethyl Diester(120033-58-1)
• EPA Substance Registry System: N-tert-Butyloxycarbonyl Glutathione DiMethyl Diester(120033-58-1)

Safety Data

• Hazardous Substances Data: 120033-58-1(Hazardous Substances Data)

Usage

Uses

Protected Glutathione (G597951). The major thiol compound of living plant and animal cells.

Upstream product

• 120033-66-1 N-(tert-butoxycarbonyl)-S-(tert-butylthio)glutathione bis(methyl ester) 
• 881390-72-3 N-(tert-butoxycarbonyl)-S-trityl glutathione dimethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 566172-19-8 bis-(N'-Boc)-L-glutathione disulfide tetramethyl ester 
• 27025-41-8 Oxidized glutathione 
• 146963-33-9 L-glutathione disulfide tetramethyl ester dihydrochloride 
• 528530-84-9 N-(tert-butoxycarbonyl)-S-trityl glutathione 
• 70-18-8 GLUTATHIONE 
• 120033-64-9 N-(t-butoxycarbonyl)-S-glutamic acid α-methyl ester γ-(4-nitrophenyl) ester 
• 120033-65-0 H-Cys(StBu)-Gly-OMe 
• 120033-61-6 N-glycine methyl ester 

Downstream Products

• 120033-44-5 S-(N-methylcarbamoyl)glutathione hydrochloride 
• 1197053-77-2 C₂₄H₃₄IN₃O₈S 
• 1407967-89-8 C₂₉H₄₃N₃O₁₀S 
• 1407967-96-7 C₅₂H₆₃N₃O₁₄S 

Relevant articles and documents

Application of dehydroalanine as a building block for the synthesis of selenocysteine-containing peptides

Selenocysteine (Sec), the 21st proteinogenic amino acid, is inserted co-translationally into number of natural proteins. It is coded by a dual function stop codon UGA (opal). It is a redox active amino acid found at the active sites of several

Preparation of N-tBoc 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-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.

Allylic selenosulfide rearrangement: A method for chemical ligation to cysteine and other thiols

Alkylation of potassium selenosulfate with allylic halides gives Se-allyl seleno Bunte salts. On reaction with thiols at room temperature, these afford mixed dialkyl selenosulfides, which undergo 2,3-sigmatropic rearrangement with loss of selenium, either spontaneously or with assistance by triphenylphosphine, thereby providing mixed dialkyl sulfides and a new permanent chemical ligation method. The process is illustrated through the lipidation of cysteine-containing tripeptides and by the allylation of 1-thioglucose tetraacetate. Copyright