The influence of 5-halo substituents on the thermal depyrimidination of the glycosidic bond in 2′-deoxyuridines

Following fusion, 2′-deoxynucleosides undergo thermolytic cleavage of the glycosidic bond to yield the corresponding base, furfuryl alcohol, and water. Purine deoxynucleosides are more readily subject to thermal cleavage of the base than are pyrimidine deoxynucleosides, such as 2′-deoxyuridine. Howe...

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Published inArchives of biochemistry and biophysics Vol. 165; no. 1; pp. 46 - 50
Main Authors Olafsson, P.G., Bryan, A.M.
Format Journal Article
LanguageEnglish
Published United States Elsevier Inc 01.11.1974
Subjects
Bromodeoxyuridine
Calorimetry
Deoxyuridine - analogs & derivatives
Floxuridine
Guanosine - analogs & derivatives
Iodine
Molecular Conformation
Temperature
Thermodynamics
Thymidine
Thymine - analogs & derivatives
Uracil - analogs & derivatives
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ISSN0003-9861
1096-0384
DOI10.1016/0003-9861(74)90139-8

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Summary:Following fusion, 2′-deoxynucleosides undergo thermolytic cleavage of the glycosidic bond to yield the corresponding base, furfuryl alcohol, and water. Purine deoxynucleosides are more readily subject to thermal cleavage of the base than are pyrimidine deoxynucleosides, such as 2′-deoxyuridine. However, when the latter deoxynucleoside is substituted by halogens in the 5-position, the glycosidic bond is weakened and loss of halouracil is competitive with ease of depurination. The reduction in strength of the glycosidic bond is linearly related to the corresponding meta Hammett substituent constant.
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ISSN:0003-9861
1096-0384
DOI:10.1016/0003-9861(74)90139-8