Convenient synthesis of 8-amino-2'-deoxyadenosine.
We studied the behaviour of 8-azido-2'-deoxyadenosine and 8-bromo-2'-deoxyadenosine in aqueous solutions of ammonia and primary and secondary amines. Unexpectedly, 8-Azido-2'-deoxyadenosine is converted to 8-amino-2'-deoxyadenosine in excellent yields. The use of this reaction for the preparation of 8-aminoadenine derivatives needed for the preparation of oligonucleotides carrying 8-aminoadenine is discussed.
Frieden
Miriam
M
Instituto de Biologia Molecular de Barcelona, C.S.I.C. Jordi Girona, Barcelona, Spain.
Aviñó
Anna
A
Eritja
Ramon
R
D000588:Amines / Q000737:chemistry; D000641:Ammonia / Q000737:chemistry; D001386:Azides / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D003839:Deoxyadenosines / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009841:Oligonucleotides; D011687:Purines / Q000737:chemistry
C113509:8-azido-2'-deoxyadenosine; D000588:Amines; D001386:Azides; D003839:Deoxyadenosines; D009841:Oligonucleotides; D011687:Purines; C090166:8-amino-2'-deoxyadenosine; C042464:8-bromo-2'-deoxyadenosine; D000641:Ammonia