Synthesis of photolabile o-nitroveratryloxycarbonyl (NVOC) protected peptide nucleic acid monomers

被引：22

作者：

Liu, ZC ^{[1
]}

Shin, DS

Lee, KT

Jun, BH

Kim, YK

Lee, YS

机构：

[1] Seoul Natl Univ, Sch Chem Engn, Seoul 151742, South Korea

[2] Seoul Natl Univ, Sch Elect Engn & Comp Sci, Seoul 151742, South Korea

来源：

TETRAHEDRON | 2005年 / 61卷 / 33期

关键词：

PNA monomers; o-nitroveratryloxycarbonyl; photolithography;

D O I：

10.1016/j.tet.2005.06.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chemical synthesis of peptide nucleic acid (PNA) monomers was accomplished using various combinations of the o-nitroveratryloxycarbonyl (NVOC) group (N-aminoethylglycine backbone) and base labile acyl-type nucleobase protecting groups (anisoyl for adenine and cytosine; isobutyryl for guanine), thus offering a photolithographic solid-phase PNA synthetic strategy compatible with photolithographic oligonucleotide synthesis conditions and allowing the in situ synthesis of PNA microarrays in an essentially neutral medium, by avoiding the use of the commonly used deprotection reagents such as trifluoroacetic acid or piperidine. Convenient methods were also explored to prepare 1-(carboxymethyl)-4-N-(4-methoxybenzoyl)cytosine and 9-(carboxymethyl)-2-N-(isobutyryl)guanine with good yields. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：7967 / 7973

页数：7

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