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Chemical Compound Review

Thiofosgen     thiophosgene

Synonyms: THIOPHOSGENE, CSCl2, CPD-8213, HSDB 861, ACMC-1AH2M, ...
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High impact information on thiophosgene

  • The two first transition metal carbonyl isothiocyanates were prepared in high yield within two steps from photolysis of CpFe(CO)2I and 3- or 4-aminophthalimide in the presence of diisopropylamine followed by reaction with thiophosgene/triethylamine [1].
  • The nitrophenyl-substituted chelators were converted to the corresponding amines by hydrogenation then reacted with thiophosgene to give the protein-reactive aryl isothiocyanate derivatives [2].
  • The trisaccharide which corresponds to a structural motif occurring in N-glycoprotein glycans from human urokinase, human recombinant protein C, phospholipase A2 as well as O-glycans, was converted into a neoglycoprotein following introduction of a cysteamine-derived spacer group and subsequent activation with thiophosgene [3].
  • The allyl glycosides were coupled with cysteamine, activated with thiophosgene and conjugated to bovine serum albumin (BSA) [4].
  • Carbonyl sulfide appears to arise from a captan-derived metabolite, thiophosgene (CSCl2), which decomposes to COS in aqueous solutions and in the presence of NADPH inhibits the activity of drug biotransformation enzymes [5].

Biological context of thiophosgene

  • A cellulose isothiocyanate has been prepared by treatment of cellulose with 2,4-di-isocyanatotoluene followed by hydrolysis and reaction of the resulting amine with thiophosgene [6].
  • After reductive amination, spacer elongation of the allyl group with cysteamine and activation with thiophosgene, the ligands were reacted with BSA [7].


  1. Cyclopentadienyl iron dicarbonyl (eta 1-N-phthalimidato) complexes containing an isothiocyanate function: synthesis and application to protein side-chain selective labeling. Kazimierczak, A., Zakrzewski, J., Salmain, M., Jaouen, G. Bioconjug. Chem. (1997) [Pubmed]
  2. Carboxymethyl-substituted bifunctional chelators: preparation of aryl isothiocyanate derivatives of 3-(carboxymethyl)-3-azapentanedioic acid, 3,12-bis(carboxymethyl)-6,9-dioxa-3,12-diazatetradecanedioic++ + acid, and 1,4,7,10-tetraazacyclododecane-N,N',N",N'''-tetraacetic acid for use as protein labels. Kline, S.J., Betebenner, D.A., Johnson, D.K. Bioconjug. Chem. (1991) [Pubmed]
  3. Synthesis of a neoglycoprotein containing the Lewis X analogous trisaccharide beta-D-GalpNAc-(1-->4)[alpha-L-Fucp-(1-->3)]-beta-D-GlcpNAc. Bartek, J., Müller, R., Kosma, P. Carbohydr. Res. (1998) [Pubmed]
  4. Synthesis and serological characterization of L-glycero-alpha-D-manno-heptopyranose-containing di- and tri-saccharides of the non-reducing terminus of the Escherichia coli K-12 LPS core oligosaccharide. Antonov, K.V., Backinowsky, L.V., Grzeszczyk, B., Brade, L., Holst, O., Zamojski, A. Carbohydr. Res. (1998) [Pubmed]
  5. Toxicologic studies of N-trichloromethylthio-4-cyclohexene-1,2-dicarboximide (captan): its metabolism by rat liver drug-metabolizing enzyme system. Peeples, A., Dalvi, R.R. Toxicology (1978) [Pubmed]
  6. Reactions of cellulose isothiocyanates with thiol and amino compounds. Gemeiner, P., Augustín, J., Drobnica, L. Carbohydr. Res. (1977) [Pubmed]
  7. A novel strategy for the synthesis of neoglycoconjugates from deacylated deep rough lipopolysaccharides. Müller-Loennies, S., Grimmecke, D., Brade, L., Lindner, B., Kosma, P., Brade, H. J. Endotoxin Res. (2002) [Pubmed]
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