title: Chemical syntheses of oligodeoxyribonucleotides containing spore photoproduct.
abstract: 5-(α-Thyminyl)-5,6-dihydrothymine, also called spore photoproduct or SP, is commonly found in the genomic DNA of UV-irradiated bacterial endospores. Despite the fact that SP was discovered nearly 50 years ago, its biochemical impact is still largely unclear due to the difficulty of preparing SP-containing oligonucleotide in high purity. Here, we report the first synthesis of the phosphoramidite derivative of dinucleotide SP TpT, which enables successful incorporation of SP TpT into oligodeoxyribonucleotides with high efficiency via standard solid-phase synthesis. This result provides the scientific community a reliable means to prepare SP-containing oligonucleotides, laying the foundation for future SP biochemical studies. Thermal denaturation studies of the SP-containing oligonucleotide found that SP destabilizes the duplex by 10-20 kJ/mol, suggesting that its presence in the spore-genomic DNA may alter the DNA local conformation.
authors.affiliation: Department of Chemistry and Chemical Biology, Indiana University-Purdue University Indianapolis, Indianapolis, Indiana 46202, USA.
authors.forename: Yajun
authors.initials: Y
authors.lastname: Jian
authors.forename: Lei
authors.initials: L
authors.lastname: Li
mesh_terms: D003854:Deoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D055668:Photochemical Processes; D013941:Thymine / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: C583508:5-(alpha-thyminyl)-5,6-dihydrothymine; D003854:Deoxyribonucleotides; D013941:Thymine