Synthesis of photolabile o-nitroveratryloxycarbonyl (NVOC) protected peptide nucleic acid monomers |
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Authors: | Zheng-Chun Liu Dong-Sik Shin Bong-Hyun Jun Yoon-Sik Lee |
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Institution: | a School of Chemical Engineering, Seoul National University, Kwanak-Gu, Seoul 151-742, South Korea b School of Electrical Engineering and Computer Science, Seoul National University, Kwanak-Gu, Seoul 151-742, South Korea |
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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. |
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Keywords: | PNA monomers o-Nitroveratryloxycarbonyl Photolithography |
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