Synthesis and properties of 7-substituted 7-deazapurine (pyrrolo[2,3-d]pyrimidine) 2'-deoxyribonucleosides.
7-Substituted 7-deazapurine (pyrrolo[2,3-d]pyrimidine) 2'-deoxyribonucleosides are synthesized by stereoselective nucleobase anion glycosylation. The introduction of a halogen at C7 is performed regioselectively either on the nucleobase or on the nucleoside. The pK(a) values of a series of 7-deazapurine 2'-deoxyribonucleosides are provided, and fluorescence properties are also discussed.
Seela
Frank
F
Universität Osnabrück, Osnabrück, Germany.
Peng
Xiaohua
X
D003853:Deoxyribonucleosides / Q000138:chemical synthesis*; D015394:Molecular Structure; D011687:Purines / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D013237:Stereoisomerism
C512929:7-deazapurine; D003853:Deoxyribonucleosides; D011687:Purines; D011743:Pyrimidines; D011758:Pyrroles; C450639:Pyrrolo(2,3-d)pyrimidine