New S-adenosyl-L-methionine analogues: synthesis and reactivity studies.
Two new and complementary synthetic strategies for 5'-N-chloroethylamino-5'-deoxyadenosines are presented. Additionally, the reaction kinetics of their conversion into aziridines under typical enzyme assay conditions is reported using time-resolved NMR spectroscopy. A stable photocaged derivative of 5'-N-chloroethylamino-5'-deoxyadenosine has also been synthesized, and its stability and activation in aqueous solution at physiological pH have been examined.
Townsend
Andrew P
AP
University of Nottingham, School of Chemistry, Centre for Biomolecular Sciences, University Park, Nottingham, NG7 2RD, United Kingdom.
Roth
Stefanie
S
Williams
Huw E L
HE
Stylianou
Eleni
E
Thomas
Neil R
NR
D001388:Aziridines / Q000138:chemical synthesis / Q000737:chemistry*; D003839:Deoxyadenosines / Q000138:chemical synthesis* / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010777:Photochemistry; D012436:S-Adenosylmethionine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship
C542535:5'-N-chloroethylamino-5'-deoxyadenosine; D001388:Aziridines; D003839:Deoxyadenosines; D012436:S-Adenosylmethionine