Ring-expanded analogues of natural oxetanocin: (+) and (-) hydroxymethyl isodideoxyadenosine.
New enantiomeric isonucleoside analogues related to natural oxetanocin have been synthesized from D-glucosamine and D-glucose. The structures of the target compounds were confirmed by NMR, HRMS, UV, single crystal X-ray, and optical rotation data. Stability studies with respect to purine nucleoside phosphorylase and adenosine deaminase show that these compounds are not substrates. Antiviral results are discussed.
Chun
Byoung-Kwon
BK
Department of Pharmaceutical and Biomedical Sciences, The University of Georgia, Athens, Georgia 30602, USA.
Vadakkan
Jean John
JJ
Nair
Vasu
V
D000225:Adenine / Q000031:analogs & derivatives* / Q000737:chemistry; D000241:Adenosine / Q000737:chemistry*; D000243:Adenosine Deaminase / Q000737:chemistry; D019380:Anti-HIV Agents / Q000494:pharmacology; D000998:Antiviral Agents / Q000494:pharmacology; D005944:Glucosamine / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D011684:Purine Nucleosides / Q000737:chemistry; D011683:Purine-Nucleoside Phosphorylase / Q000737:chemistry; D013237:Stereoisomerism; D014466:Ultraviolet Rays; D014965:X-Rays
D019380:Anti-HIV Agents; D000998:Antiviral Agents; D011684:Purine Nucleosides; C051061:oxetanocin; D011683:Purine-Nucleoside Phosphorylase; D000243:Adenosine Deaminase; D005947:Glucose; D000225:Adenine; D000241:Adenosine; D005944:Glucosamine