Open AccessDNA ligation using photoremovable protecting groups
Author(s) -
Yawara Kawano,
Tadao Takada,
Mitsunobu Nakamura,
Kazushige Yamana
Publication year - 2009
Publication title -
nucleic acids symposium series
Language(s) - Uncategorized
Resource type - Journals
eISSN - 1746-8272
pISSN - 0261-3166
DOI - 10.1093/nass/nrp087
Subject(s) - thiol , oligonucleotide , native chemical ligation , ligation , chemistry , dna , protecting group , functional group , chemical ligation , combinatorial chemistry , disulfide bond , cysteine , biochemistry , organic chemistry , microbiology and biotechnology , biology , enzyme , alkyl , polymer
Template-directed ligation of oligonucleotides by photochemical reaction has attracted much interest because of its biomedical and synthetic applications. In this study, we developed photoligaton of DNA by using a photoremovable protecting group and thiol-disulfide exchange reaction. A phosphoroamidite of o-nitrobenzyl derivatives were synthesized, and DNA modified with a nitrobenzyl-protected thiol group and disulfide group was synthesized by conventional phosphoroamidite chemistry using a DNA synthesizer. It was shown that photochemical reaction of a nitrobenzyl group with UV irradiation produced a free thiol group, leading to the DNA ligation through the thiol-disulfide exchange reaction.
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