Development of a new method for the synthesis of oligodeoxynucleotides by use of carbamoyl-type protecting groups.
Previously, we observed thermal elimination of a quinolylcarbamoyl group from N-quinolylcarbamoylated nucleobase residues. In this paper, we examined the thermal stability of several carbamoyl groups on nucleobases and developed new carbamoyl-type protecting groups for base protection that can be removed by "heating". Particularly, the phenylsulfonylcarbamoyl group was found to be rapidly removed from three kinds of nucleobases, cytosine, adenine, and guanine bases. Moreover, we could carry out the synthesis of oligodeoxynucleotides by using the thermolytic protecting group for base protection.
Ohkubo
Akihiro
A
Department of Life Science, Tokyo Institute of Technology, 4259 Nagatsuta, Midoriku, Yokohama, 2268501, Japan.
Kasuya
Rintaro
R
Miyata
Kenichi
K
Taguchi
Haruhiko
H
Seio
Kohji
K
Sekine
Mitsuo
M
D000225:Adenine / Q000737:chemistry; D001671:Biochemistry / Q000379:methods; D003596:Cytosine / Q000737:chemistry; D006147:Guanine / Q000737:chemistry; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry*; D013696:Temperature
D009838:Oligodeoxyribonucleotides; D013449:Sulfonamides; D006147:Guanine; D003596:Cytosine; D000225:Adenine