3'-Beta-ethynyl and 2'-deoxy-3'-beta-ethynyl adenosines: first 3'-beta-branched-adenosines substrates of adenosine deaminase.
The 3'-C-branched-adenosine and 2'-deoxyadenosine analogues 1-7 were tested as substrate of adenosine deaminase. The 9-(3'-C-ethynyl-beta-D-ribo-pentofuranosyl)adenine 1 and its 2'-deoxy analogue 7 were deaminated by the enzyme while the vinyl and ethyl derivatives 2 and 3 were not. The 9-(3'-C-branched-beta-D-xylo-pentofuranosyl)adenines 4-6 were deaminated by the deaminase.
Tritsch
D
D
Laboratoire de Chimie Organique Biologique UMR 7509 du CNRS, Université Louis Pasteur, Faculté de Chimie, Strasbourg, France. dtritsch@chimie.u-strasbg.fr
Jung
P M
PM
Burger
A
A
Biellmann
J F
JF
D000241:Adenosine / Q000031:analogs & derivatives* / Q000378:metabolism; D000243:Adenosine Deaminase / Q000378:metabolism*; D003839:Deoxyadenosines / Q000378:metabolism; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009705:Nucleosides / Q000737:chemistry* / Q000378:metabolism; D013379:Substrate Specificity
D003839:Deoxyadenosines; D009705:Nucleosides; D000243:Adenosine Deaminase; D000241:Adenosine