期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 27, 页码 7001-7005出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201310609
关键词
click chemistry; cycloaddition; DNA cross-linking; nucleosides; photoswitch
资金
- National Cancer Institute [1R15CA152914-01]
- UWM Research Growth Initiative [RGI101X234]
- WiSys technology foundation
- Great Milwaukee Foundation
- National Institute of Environmental Health Sciences [R01 ES019873]
A coumarin-modified pyrimidine nucleoside (1) has been synthesized using a Cu-I-catalyzed click reaction and incorporated into oligodeoxynucleotides (ODNs). Interstrand cross-links are produced upon irradiation of ODNs containing 1 at 350 nm. Cross-linking occurs through a [2+2] cycloaddition reaction with the opposing thymidine, 2'-deoxycytidine, or 2'-deoxyadenosine. A much higher reactivity was observed with dT than dC or dA. Irradiation of the dT-1 and dC-1 cross-linked products at 254 nm leads to a reversible ring-opening reaction, while such phenomena were not observed with dA-1 adducts. The reversible reaction is ultrafast and complete within 50-90 s. Consistent photoswitching behavior was observed over 6 cycles of irradiation at 350 nm and 254 nm. To the best of our knowledge, this is the first example of photoswitchable interstrand cross-linking formation induced by a modified pyrimidine nucleoside.
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