TY - JOUR
T1 - Deglycosylation of alkylated nucleosides: A molecular orbital study
AU - Venkateswarlu, Divi
AU - Lyngdoh, R.H. Duncan
PY - 1997/11/10
Y1 - 1997/11/10
N2 - The glycoside bond in alkylated nucleosides is known to be more stable for O6-alkylguanosines and O4-alkylthymines, and less stable for N3- and N7-alkylpurine and O2-alkylpyrimidine nucleosides. These marked differences have been demonstrated through in vitro acidic hydrolysis and in vivo glycosylase repair. This study examines the relative facility of the deglycosylation reaction for various nucleosides through the use of theoretical indices derived from the semiempirical AM1 SCF-MO methodology, which furnish inferences much in consonance with experiment. © 1997 Elsevier Science B.V.
AB - The glycoside bond in alkylated nucleosides is known to be more stable for O6-alkylguanosines and O4-alkylthymines, and less stable for N3- and N7-alkylpurine and O2-alkylpyrimidine nucleosides. These marked differences have been demonstrated through in vitro acidic hydrolysis and in vivo glycosylase repair. This study examines the relative facility of the deglycosylation reaction for various nucleosides through the use of theoretical indices derived from the semiempirical AM1 SCF-MO methodology, which furnish inferences much in consonance with experiment. © 1997 Elsevier Science B.V.
KW - Alkylated nucleosides
KW - Deglycosylation
KW - In vitro stability
KW - Molecular orbital calculations
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U2 - 10.1016/S0166-1280(97)00063-8
DO - 10.1016/S0166-1280(97)00063-8
M3 - Article
SN - 0166-1280
VL - 418
SP - 49
EP - 57
JO - Journal of Molecular Structure: THEOCHEM
JF - Journal of Molecular Structure: THEOCHEM
IS - 1
ER -