Deglycosylation of alkylated nucleosides: A molecular orbital study

Divi Venkateswarlu; R. H.Duncan Lyngdoh

doi:10.1016/S0166-1280(97)00063-8

Deglycosylation of alkylated nucleosides: A molecular orbital study

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	49-57
Number of pages	9
Journal	Journal of Molecular Structure: THEOCHEM
Volume	418
Issue number	1
DOIs	https://doi.org/10.1016/S0166-1280(97)00063-8
State	Published - Nov 10 1997
Externally published	Yes

Keywords

Alkylated nucleosides
Deglycosylation
In vitro stability
Molecular orbital calculations

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10.1016/S0166-1280(97)00063-8

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title = "Deglycosylation of alkylated nucleosides: A molecular orbital study",

abstract = "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.",

keywords = "Alkylated nucleosides, Deglycosylation, In vitro stability, Molecular orbital calculations",

author = "Divi Venkateswarlu and Lyngdoh, \{R. H.Duncan\}",

year = "1997",

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day = "10",

doi = "10.1016/S0166-1280(97)00063-8",

language = "English",

volume = "418",

pages = "49--57",

journal = "Journal of Molecular Structure: THEOCHEM",

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TY - JOUR

T1 - Deglycosylation of alkylated nucleosides

T2 - 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.

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.

KW - Alkylated nucleosides

KW - Deglycosylation

KW - In vitro stability

KW - Molecular orbital calculations

UR - https://www.scopus.com/pages/publications/0008043375

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 -

Deglycosylation of alkylated nucleosides: A molecular orbital study

Abstract

Keywords

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