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Volumn 38, Issue 12, 1997, Pages 2149-2152

Cobalt assisted cleavage of S-S bonds and a base-free synthesis of mercapturic acids

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCYSTEINE DERIVATIVE; COBALT;

EID: 0031585051     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00268-2     Document Type: Article
Times cited : (62)

References (30)
  • 3
    • 0001097869 scopus 로고
    • Trost, B.M.; Fleming, I. Eds.; Pergamon: Oxford
    • (c) Solladie, G. Comphrehensive Org. Synth. Trost, B.M.; Fleming, I. Eds.; Pergamon: Oxford, 1991, Vol.6, 133-170.
    • (1991) Comphrehensive Org. Synth. , vol.6 , pp. 133-170
    • Solladie, G.1
  • 19
    • 0021778327 scopus 로고
    • 8. Mercapturic acids are S-alkylated derivatives of N-acetyl-L-cysteine. The biosynthesis of mercapturic acids involves reaction of an electrophile with the sulfbydryl group of glutathione (..-Glu-Cys-Gly) followed by enzymatic hydrolysis of the Glu-Cys and Cys-Gly bonds and N-acetylation. Contemporary interests in mercapturic acids derives largely from the fact that their excretion implies the previous presence in the animal of an electrophile, many of which have been associated with toxic effects on living cells. Since these acids are not readily available general methods for their preparation, as authentic standards, is of interest, please see: (a) Mannervick, B. Adv. Enzymol. Relat. Areas Mol. Biol. 1985, 57, 357-406.
    • (1985) Adv. Enzymol. Relat. Areas Mol. Biol. , vol.57 , pp. 357-406
    • Mannervick, B.1
  • 22
    • 0011227933 scopus 로고    scopus 로고
    • note
    • 10. Zinc dust (3mM) was added to a degassed solution of PhSSPh (2mM) and cobalt(II)chloride (0.2mM) dissolved in MeCN (5mL) and the system flushed with nitrogen. Halide (4.2mM) in degassed MeCN (5mL) was administered dropwise and the mixture stirred at room temperature. On completion (0.5-8h; TLC inf.) MeCN was removed under reduced pressure and the mixture purified by column cbromatography (silica-gel 60-120, eluent: hexane-EtOAc, 95:5) to obtain pure sulfides.
  • 23
    • 0011159945 scopus 로고    scopus 로고
    • note
    • 2Br.
  • 24
    • 0011200377 scopus 로고    scopus 로고
    • note
    • 12. It is interesting to note that while In, Sn, Sm can cleave disulfide bond. Zn, Tl, Ga cannot, see ref. 2a.
  • 30
    • 0011226437 scopus 로고    scopus 로고
    • note
    • 2S was bubbled through the solution whence a black precipitate was obtained. This precipitate was filtered, filtrate saturated with sodiumchloride and extracted with ethylacetate at 50°C. The organic layer was dried with magnesium sulfate, concentrated and the residue purified by column chromatography [silica-gel 60-120, eluent: benzene:methanol: aceticacid - 7:2:1] to obtain the desired mercapturic acid. For benzoyl chloride reaction was worked up after 4 hrs.


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