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

Authors
Liu, ZCShin, DSLee, KTJun, BHKim, YKLee, YS
Issue Date
Aug-2005
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Keywords
PNA monomers; o-nitroveratryloxycarbonyl; photolithography
Citation
TETRAHEDRON, v.61, no.33, pp 7967 - 7973
Pages
7
Journal Title
TETRAHEDRON
Volume
61
Number
33
Start Page
7967
End Page
7973
URI
https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/148745
DOI
10.1016/j.tet.2005.06.002
ISSN
00404020
Abstract
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.
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