Synthesis of two stable nitrogen analogues of S-adenosyl-L-methionine

MJ Thompson, A Mekhalfia, DP Hornby…

Index: Thompson, Mark J.; Mekhalfia, Abdelaziz; Hornby, David P.; Blackburn, G. Michael Journal of Organic Chemistry, 1999 , vol. 64, # 20 p. 7467 - 7473

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Citation Number: 34

Abstract

Homochiral syntheses of two stable nitrogen analogues of S-adenosyl-l-methionine (AdoMet) are described. In the first analogue, AzaAdoMet, the sulfonium center of AdoMet, is replaced by an N-methyl moiety whose p K a is 7.08. This provides a charge-switchable analogue of AdoMet whose ionic state is a function of the pH. A second analogue, MeAzaAdoMet, has a quaternary dimethylammonium group in place of the ...