Synthesis of an alpha-aminophosphonate nucleoside as an inhibitor of S-adenosyl-L-homocysteine hydrolase.
A phosphonic acid analogue of S-adenosyl-L-homocysteine was prepared by a novel method and the epimeric mixture separated. Preliminary studies indicate that each epimer causes time-dependent inactivation of S-adenosyl-L-homocysteine hydrolase, however each presented distinct kinetic characteristics.
Steere
Jennifer A
JA
Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1.
Sampson
Peter B
PB
Honek
John F
JF
D000241:Adenosine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*; D043383:Adenosylhomocysteinase; D000818:Animals; D015195:Drug Design; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D006867:Hydrolases / Q000037:antagonists & inhibitors*; D007700:Kinetics; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000494:pharmacology*; D051381:Rats; D011994:Recombinant Proteins; D012435:S-Adenosylhomocysteine / Q000031:analogs & derivatives* / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C456409:5'-deoxy-5'-((3-amino-3-phosphonopropyl)thio)adenosine; D004791:Enzyme Inhibitors; D063065:Organophosphonates; D011994:Recombinant Proteins; D012435:S-Adenosylhomocysteine; D006867:Hydrolases; D043383:Adenosylhomocysteinase; D000241:Adenosine