Dealkylation of quaternary ammonium salts by thiolate anions: A model of the cobalaminindependent methionine synthase reaction. Hilhorst, E.; Chen, T.B.R.A.; Iskander, A.S.; Pandit, U.K. Disclaimer/Complaints regulationsIf you believe that digital publication of certain material infringes any of your rights or (privacy) interests, please let the Library know, stating your reasons. In case of a legitimate complaint, the Library will make the material inaccessible and/or remove it from the website. Please Ask the Library: http://uba.uva.nl/en/contact, or a letter to: Library of the University of Amsterdam, Secretariat, Singel 425, 1012 WP Amsterdam, The Netherlands. You will be contacted as soon as possible. Abstract: The reactions of thiolate ions derived from thiophenol and homocysteioe with substituted quatemary ammoniom salts result in alkyl tmnsfer from nitrogen to sulfur. A radical mechanism for this tmnsakylation, accounts for the reactivity pattern of the substrate salts. In a model study of the cobalamin-independent methionine synthase reaction, 5,5.6,7-tetramerhyl-5.6;7,8-tetrahydroptcridiniumsalt(25),whichcanbcconsidaedasamodelf~thenaMalUxxEymc 5-CH$-I4-folate (1). was allowed to react with the thiilate of homocysteiae, whereupon the won of m&ion& was observed in good yield. 'These results suggest that in the enzymatic prcnxss the N(S)-CH3 bond may be activated for the methyl transfer step, by uxndination of the N(5) with an electmphde or a proton at the active site.

Model for the cobalamin-dependent methionine synthase reaction.Hilhorst, E.; Iskander, A.S.; Chen, T.B.R.A.; Pandit, U.K.

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