TY - JOUR
T1 - A new odorless procedure for the synthesis of 2'-deoxy-6-thioguanosine and its incorporation into oligodeoxynucleotides
AU - Onizuka, Kazumitsu
AU - Taniguchi, Yosuke
AU - Sasaki, Shigeki
N1 - Funding Information:
Received 3 March 2009; accepted 17 June 2009. This work was supported by a Grant-in-Aid for Scientific Research (A) from the Japan Society for the Promotion of Science (JSPS), and CREST from the Japan Science and Technology Agency. We thank Research Fellowship of the Japan Society for the Promotion of Science (JSPS) for Young Scientists (K.O.). Address correspondence to Shigeki Sasaki, Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka812-8582, Japan. E-mail: sasaki@phar.kyushu-u.ac.jp
PY - 2009/8
Y1 - 2009/8
N2 - 6-S-[2-[(2-ethylhexyl)oxycarbonyl]ethyl)}-3',5'-O-bis(tert- butyldimethylsilyl)-2'-deoxy-6-thiogua nosine (2) was synthesized in high yield from the corresponding 6-O-mesitylenesulfonyl derivative by the reaction with 2-ethylhexyl 3-mercapto-propionate. The phosphoramidite precursor derived from 2 was successfully applied to an automated DNA synthesizer to produce 2'-deoxy-6-thioguanosine containing ODN. The results showed that 2-ethylhexyl 3-mercaptopropionate is useful as an odor less reagent and also as an S-protecting group of 2'-deoxy-6-thioguanosine.
AB - 6-S-[2-[(2-ethylhexyl)oxycarbonyl]ethyl)}-3',5'-O-bis(tert- butyldimethylsilyl)-2'-deoxy-6-thiogua nosine (2) was synthesized in high yield from the corresponding 6-O-mesitylenesulfonyl derivative by the reaction with 2-ethylhexyl 3-mercapto-propionate. The phosphoramidite precursor derived from 2 was successfully applied to an automated DNA synthesizer to produce 2'-deoxy-6-thioguanosine containing ODN. The results showed that 2-ethylhexyl 3-mercaptopropionate is useful as an odor less reagent and also as an S-protecting group of 2'-deoxy-6-thioguanosine.
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U2 - 10.1080/15257770903155576
DO - 10.1080/15257770903155576
M3 - Article
C2 - 20183614
AN - SCOPUS:75149167416
SN - 1525-7770
VL - 28
SP - 752
EP - 760
JO - Nucleosides, Nucleotides and Nucleic Acids
JF - Nucleosides, Nucleotides and Nucleic Acids
IS - 8
ER -