Synthesis of oligonucleotides containing site-specific carcinogen adducts. Preparation of the 2-cyanoethyl N,N-diisopropylphosphoramidite of N-(2′-deoxyguanosin-8-yl)-2-(acetylamino)fluorene with Fmoc as the base-protecting group
Synthesis of oligonucleotides containing site-specific carcinogen adducts. Preparation of the 2-cyanoethyl N,N-diisopropylphosphoramidite of N-(2′-deoxyguanosin-8-yl)-2-(acetylamino)fluorene with Fmoc as the base-protecting group
复制标题
含有位点特异性致癌物加合物的寡核苷酸的制备以Fmoc作为碱基保护基团的N-(2-脱氧鸟苷-8-基)-2-(乙酰氨基)芴的2-氰乙基N,N-二异丙基亚磷酰胺。
DOI：
10.1021/jo00082a011
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发表时间：
1994
影响因子：
3.6
通讯作者：
L. Romano
中科院分区：
文献类型：
--
作者：
Yuanzhong Zhou;S. Chládek;L. Romano
用9-芴甲氧羰基（Fmoc）保护N-（2 ′-脱氧鸟苷-8-基）-2-（乙酰氨基）芴（dG-Cs-AAF）修饰鸟嘌呤上的环外胺，从而制备含有位点特异性AAF加合物的寡核苷酸。Fmoc-Cl与dG-Cg-AAF反应生成N-[N-（9-芴甲氧羰基）-2 '-脱氧鸟苷-8-基]-2-乙酰氨基芴（N2-Fmoc-dG-C8-AAF）和N-[O 6 -（9-芴甲氧羰基）-2'-脱氧鸟苷-8-基]-2-乙酰氨基芴（O 6 -Fmoc-dG-Cg-AAF）。N2-Fmoc-dG-C8-AAF的5 ′-OH用4，4 ′-二甲氧基三苯甲基氯保护，得到5 ′-DMT-N2-Fmoc-dG-C8-AAF，然后将其与2-氰乙基N，N，N ′，N ′-四异丙基亚磷酰胺反应，得到相应的亚磷酰胺。也类似地制备Fmoc保护的dA、dC和dG的亚磷酰胺。研究了Fmoc保护的C8-AAF修饰的脱氧鸟苷在不同条件下的稳定性，以确定所制备的亚磷酰胺在固相DNA合成中的实用性
A 9-fluorenylmethoxycarbonyl (Fmoc) group was used to protect the exocyclic amine on the modified guanine of N-(2'-deoxyguanosin-8-yl)-2-(acetylamino)fluorene (dG-Cs-AAF) so that oligonucleotides containing a site-specific AAF adduct could be prepared. Reaction of Fmoc-Cl with dG-Cg-AAF gave N-[N-(9-fluorenylmethoxycarbonyl)-2'-deoryguanosin-8-yl]-2-(acetylamino)fluorene (N 2 -Fmoc-dG-C 8 -AAF) and N-[O 6 -(9-fluorenylmethoxycarbonyl)-2'-deoxyguanosin-8-yl]-2-(acetylamino)fluorene (O 6 -Fmoc-dG-Cg-AAF). The 5'-OH of N 2 -Fmoc-dG-C 8 -AAF was protected using 4,4'-dimethoxytrityl chloride to yield 5'-DMT-N 2 -Fmoc-dG-C 8 -AAF which was then reacted with 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite to obtain the corresponding phosphoramidite. The phosphoramidites of Fmoc-protected dA, dC and dG were also prepared similary. The stability of Fmoc-protected C 8 -AAF-modified deoxyguanosine was studied under different conditions to establish the utility of the prepared phosphoramidite of the prepared phosphoramidite in solid-phase DNA synthesis