Regioselective syntheses of 7-nitro-7-deazapurine nucleosides and nucleotides for efficient PCR incorporation.
Substitution at the C(7) position of purine nucleotides by a potent electron-withdrawing nitro group facilitates the cleavage of glycosidic bonds under alkaline conditions. This property is useful for sequence-specific cleavage of DNA containing these analogues. Here we describe the preparation of 7-deaza-7-NO(2)-dA and 7-deaza-7-NO(2)-dG using two different approaches, starting from 2'-deoxy-adenosine and 6-chloro-7-deaza-guanine, respectively. These modified nucleosides were converted to nucleotide triphosphates, each of which can replace the corresponding, naturally occurring triphosphate to support PCR amplification. [structure: see text]
Kawate
Tomohiko
T
Variagenics Inc., Cambridge, MA 02139, USA.
Allerson
Charles R
CR
Wolfe
Jia Liu
JL
D004247:DNA / Q000737:chemistry; D003838:Deoxyadenine Nucleotides / Q000138:chemical synthesis*; D003848:Deoxyguanine Nucleotides / Q000138:chemical synthesis*; D015394:Molecular Structure; D011684:Purine Nucleosides / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C511471:7-deaza-7-nitro-dATP; C511472:7-deaza-7-nitro-dGTP; D003838:Deoxyadenine Nucleotides; D003848:Deoxyguanine Nucleotides; D011684:Purine Nucleosides; D004247:DNA