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

Autor:	Yoon-Sik Lee, Bong-Hyun Jun, Zheng-Chun Liu, Yong-Kweon Kim, Kyu-Teak Lee, Dong-Sik Shin
Rok vydání:	2005
Předmět:	Peptide nucleic acid Guanine Stereochemistry Organic Chemistry Oligonucleotide synthesis Biochemistry Chemical synthesis Nucleobase chemistry.chemical_compound chemistry Drug Discovery Trifluoroacetic acid Piperidine Cytosine
Zdroj:	Tetrahedron. 61:7967-7973
ISSN:	0040-4020
DOI:	10.1016/j.tet.2005.06.002
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::dcbe9404484759e5b7131db43ebebde9 https://doi.org/10.1016/j.tet.2005.06.002 Zobrazit plný text záznamu Full Text from ScienceDirect