Synthesis of a thymine glycol building block and its incorporation into oligonucleotides.
A phosphoramidite building block of thymine glycol, a major oxidative base damage in DNA, was synthesized in four steps from protected thymidine. The two hydroxyl functions of the oxidized base were protected with the tert-butyldimethylsilyl group. Using this building block, oligonucleotides containing this damage were synthesized.
Iwai
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Biomolecular Engineering Research Institute, 6-2-3 Furuedai, Suita, Osaka 565-0874, Japan.
D001483:Base Sequence; D002851:Chromatography, High Pressure Liquid; D004249:DNA Damage; D008722:Methods; D015394:Molecular Structure; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D009993:Osmium Tetroxide; D010084:Oxidation-Reduction; D013941:Thymine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*
D009838:Oligodeoxyribonucleotides; C029389:thymine glycol; D009993:Osmium Tetroxide; D013941:Thymine