Improved synthesis of 2'-amino-2'-deoxyguanosine and its phosphoramidite.
2'-Amino-2'-deoxynucleosides and oligonucleotides containing them have proven highly effective for an array of biochemical applications. The guanosine analogue and its phosphoramidite derivatives have been accessed previously from 2'-amino-2'-deoxyuridine by transglycosylation, but with limited overall efficiency and convenience. Using simple modifications of known reaction types, we have developed useful protocols to obtain 2'-amino-2'-deoxyguanosine and two of its phosphoramidite derivatives with greater convenience, fewer steps, and higher yields than reported previously. These phosphoramidites provide effective synthons for the incorporation of 2'-amino-2'-deoxyguanosine into oligonucleotides.
Dai
Qing
Q
Howard Hughes Medical Institute, The University of Chicago, MC 1028, Chicago, IL 60637, USA.
Deb
Shirshendu K
SK
Hougland
James L
JL
Piccirilli
Joseph A
JA
D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008722:Methods; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry
D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; C014319:2'-amino-2'-deoxyguanosine; D003849:Deoxyguanosine