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 in | Archives of biochemistry and biophysics Vol. 165; no. 1; pp. 46 - 50 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
United States
Elsevier Inc
01.11.1974
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| Subjects | |
| Online Access | Get full text |
| ISSN | 0003-9861 1096-0384 |
| DOI | 10.1016/0003-9861(74)90139-8 |
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| Abstract | 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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| AbstractList | 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. |
| Author | Bryan, A.M. Olafsson, P.G. |
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| Cites_doi | 10.1021/jo01345a033 10.1002/jps.2600520531 10.1021/jo01103a606 10.1016/0014-3057(67)90056-0 10.1021/bi00751a005 10.1021/bi00833a004 10.1021/ja01074a044 10.1135/cccc19622550 10.1016/S0040-4020(01)83405-0 10.1016/S0022-2836(62)80046-1 10.1135/cccc19593154 10.1016/S0008-6215(00)85726-2 |
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| Snippet | Following fusion, 2′-deoxynucleosides undergo thermolytic cleavage of the glycosidic bond to yield the corresponding base, furfuryl alcohol, and water. Purine... |
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| SubjectTerms | Bromodeoxyuridine Calorimetry Deoxyuridine - analogs & derivatives Floxuridine Guanosine - analogs & derivatives Iodine Molecular Conformation Temperature Thermodynamics Thymidine Thymine - analogs & derivatives Uracil - analogs & derivatives |
| Title | The influence of 5-halo substituents on the thermal depyrimidination of the glycosidic bond in 2′-deoxyuridines |
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