用于2'-修饰寡核苷酸固相合成和化学选择性连接的1,2 -二醇和酰肼亚磷酰胺

1,2-Diol and hydrazide phosphoramidites for solid-phase synthesis and chemoselective ligation of 2'-modified oligonucleotides.

作者信息

Zubin Eugeny M, Stetsenko Dmitry A, Oretskaya Tatiana S, Gait Michael J

机构信息

Chemistry Department and A.N. Belozersky Institute of Physico-Chemical Biology, M.V. Lomonosov Moscow State University, Moscow, Russia.

出版信息

Nucleosides Nucleotides Nucleic Acids. 2003 May-Aug;22(5-8):1375-8. doi: 10.1081/NCN-120022969.

DOI:10.1081/NCN-120022969

PMID:14565422

Abstract

The preparation of two novel 2'-O-alkyl phosphoramidites bearing 1,2-diol and hydrazide functions for a chemoselective ligation is described. The former amidite was used to obtain 2'-modified oligodeoxyribonucleotides, which can be later oxidised by NaIO4 to generate 2'-aldehyde oligonucleotides. These were successfully conjugated to acceptor molecules. The latter amidite also showed good coupling yields, but the hydrazide function was demonstrated to be labile under basic deprotection conditions.

摘要

描述了两种带有1,2 -二醇和酰肼官能团的新型2'-O-烷基亚磷酰胺的制备，用于化学选择性连接。前一种亚磷酰胺用于获得2'-修饰的寡脱氧核糖核苷酸，其随后可被高碘酸钠氧化以生成2'-醛基寡核苷酸。这些已成功与受体分子共轭。后一种亚磷酰胺也显示出良好的偶联产率，但酰肼官能团在碱性脱保护条件下被证明是不稳定的。