A simple method for C-6 modification of guanine nucleosides.
A facile method for the introduction of various substituents at the C-6 position of guanosine and 2'-deoxyguanosine is reported. In a simple, 1-step transformation, tert-butyldimethylsilyl protected guanosine and 2'-deoxyguanosine were converted to the O(6)-(benzotriazol-1-yl) derivatives via reaction with 1H-benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and 1,8-diazabicyclo[5.4.0]undec-7ene (DBU). The easily isolated, stable and storable, O(6)-(benzotriazol-1-yl) guanosine derivatives upon exposure to a range of nucleophiles, under appropriate conditions, led to the C-6 modified 2-amino purine nucleoside analogues in good yields.
Lakshman
Mahesh K
MK
Department of Chemistry, The City College and The City University of New York, 160 Convent Avenue, New York, NY 10031-9198, USA. lakshman@sci.ccny.cuny.edu
Frank
Josh
J
D000588:Amines / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D006147:Guanine / Q000737:chemistry*; D011684:Purine Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry
D000588:Amines; D011684:Purine Nucleosides; D014230:Triazoles; D006147:Guanine; D002244:Carbon