Stereoselective synthesis of a novel apio analogue of neplanocin A as potential S-adenosylhomocysteine hydrolase inhibitor.
A total synthesis of apio-neplanocin A, which combines properties of apio nucleoside and neplanocin A and is a potential inhibitor of S-adenosylhomocysteine hydrolase, was accomplished starting from D-ribose via stereoselective hydroxymethylation and RCM reaction. [reaction: see text]
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D043383:Adenosylhomocysteinase; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry*; D006867:Hydrolases / Q000037:antagonists & inhibitors*; D015394:Molecular Structure; D013237:Stereoisomerism
D004791:Enzyme Inhibitors; C031096:neplanocin A; D006867:Hydrolases; D043383:Adenosylhomocysteinase; D000241:Adenosine