Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 7, Pages 3021-3029Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo400013n
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Funding
- National Institutes of Health [R00ES017177]
- IUPUI RSFG
- IUCRG
- IUPUI
- National Science Foundation MRI [CHE-0619254, DBI-0821661]
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5-(alpha-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 SO 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.
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