Synthesis of Two Stable Nitrogen Analogues of S-Adenosyl-l-methionine

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 pK a is 7.08. This provides a charge-switchable analogue of AdoMet whose ionic state is a...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 64; no. 20; pp. 7467 - 7473
Main Authors Thompson, Mark J, Mekhalfia, Abdelaziz, Hornby, David P, Blackburn, G. Michael
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.10.1999
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ADENOSYLMETHIONINE
PEPTIDES
REMOVAL
ACID
ESTERS
CATALYTIC TRANSFER HYDROGENATION
PROTECTING GROUPS
REPRESSOR
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Summary: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 pK 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 methylsulfonium center of AdoMet:  thus, its ionic state is independent of pH.
Bibliography:istex:1A46597FF0EF3DBC66AFE901077189CED31585A0
ark:/67375/TPS-P8F7QZ1L-Q
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9907742