Chemical and Pharmaceutical Bulletin p. 2231 - 2237 (1994)
Update date:2022-08-11
Topics:
Ono
Okamoto
Inada
Nara
Matsuda
Thymidine was converted into 5-formyl-2'-deoxyuridine (1), which was incorporated into oligonucleotides, 5'd(GGAGA1CTCC)3' (I-1) and 5'd(GCTGC1GCGAAAGCTG)3' (II-1). To avoid side-reactions and degradation, protection of the formyl group of 1 using a newly developed protecting group, N,N-di-(3,5-dichlorophenyl)ethylenediamine, was necessary. Compound 1 was unstable under the conditions employed for enzymatic complete digestion of oligonucleotides, so that a peak corresponding to 1 was not detected clearly by HPLC analysis of a nucleoside mixture obtained by complete hydrolysis of I-1. Therefore, the oligonucleotide I-1 was treated with cyanomethylenetriphenylphosphorane to give an oligonucleotide containing (E) and (Z)-5-(2-cyanovinyl)-2'-deoxyuridine, which was then hydrolyzed, and the newly generated nucleosides were detected by HPLC analysis. The T(m) of the self-complementary oligonucleotide I-1 (40 °C) was higher than that of the parent oligonucleotide, 5'd(GGAGATCTCC)3', (31 °C) in a buffer containing 0.01 M sodium phosphate (pH 7.0) and 0.1 M NaCl. DNA replication study on a template-primer system [primer, 5'd(32P-CAGCTTTCGC)3'; template, 3'd(GTCGAAAGCGXCGTCG)5' (X=1 or T)] showed that dATP was incorporated into the DNA strand at a site opposite to 1 by Klenow DNA polymerase, but with a reduced rate. The formyl group of 1 in the oligonucleotides reacted with amines to give Schiff base derivatives. oligonucleotide synthesis; 5-formyluracil
View MoreJintan Jinnuo Chemical Co., Ltd.
Contact:+86-519-80199901
Address:Room 1804, Building 1, Huacheng Business Plaza, Jintan, Jiangsu, China
website:http://www.sigmaaldrich.com
Contact:800 558-9160
Address:Industriestrasse 25CH-9471 Buchs SGSwitzerland
Beijing Mashi Fine Chemical Co.,Ltd.
Contact:+86-10-61271592
Address:Room 506, Section B, Kaichi Mansion, Industrial Development
Contact:86-571-86737118-8689
Address:No.69, 12 Street, HEDA, Hangzhou, Zhejiang, China
Jinan Decheng Hemu Medical Technology Co.,Ltd.
Contact:+86-531-68650525
Address:NO.554 Zhengfeng Road High-new Technology Development Zone
Doi:10.1021/acs.joc.5b01875
(2015)Doi:10.1021/acs.orglett.9b03853
(2019)Doi:10.1039/c4dt03206c
(2015)Doi:10.1016/S0039-128X(81)80016-5
(1981)Doi:10.1021/acs.analchem.6b01603
(2016)Doi:10.1039/jr9650007094
(1965)