高效合成含 5-羟甲基胞嘧啶的 DNA。

Efficient synthesis of 5-hydroxymethylcytosine containing DNA.

机构信息

Center for Integrated Protein Science, Department of Chemistry, Ludwig-Maximilians-University Munich, Butenandtstr. 5-13, 81377 Munich, Germany.

出版信息

Org Lett. 2010 Dec 17;12(24):5671-3. doi: 10.1021/ol102408t. Epub 2010 Nov 17.

DOI:10.1021/ol102408t

PMID:21082782

Abstract

5-Hydroxymethylcytosine ((5-HOMe)dC) was recently discovered as the sixth base in the mammalian genome. The development of a new phosphoramidite building block is reported, which allows efficient synthesis of (5-HOMe)dC containing DNA. Key steps of the synthesis are a palladium-catalyzed formylation and the simultaneous protection of a hydroxyl and amino group as a cyclic carbamate. DNA synthesis is possible under standard conditions, and deprotection can be carried out with dilute NaOH.

摘要

5-羟甲基胞嘧啶((5-HOMe)dC)最近被发现是哺乳动物基因组中的第六种碱基。本文报道了一种新的亚磷酰胺碱基砌块的开发，该砌块可高效合成含(5-HOMe)dC 的 DNA。合成的关键步骤是钯催化的甲酰化以及羟基和氨基的同时保护作为环状碳酸酯。在标准条件下可以进行 DNA 合成，并且可以用稀氢氧化钠进行脱保护。