As substitutes for antisense and triplex oligonucleotides, oligopeptides containing N~-(thymin-l-ylacetyl) 13-aminoalanine and NO-(cytosin-l-ylacetyl) 13-aminoalanine moieties were synthesized on solid support by using standard Boc-chemistry. The obtained peptide containing ten thymine bases was sh
Nucleic acid analog peptide (NAAP). Solid phase synthesis of a DNA analog peptide
โ Scribed by Masayuki Fujii; Koji Yamamoto; Jinsai Hidaka; Takayuki Ohtsu
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 174 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
Solid phase synthesis of a nucleic acid analog peptide (NAAP), as a substitute for antisense or triple-helix forming oligonucleotide, is described. The N-protected amino acid monomer was prepared starting from 3'-azido-3'-deoxythymidine (AZT) in 20 % overall yield. Condensation of the amino acid monomer was performed using Boc-chemistry on MBHA resin to afford a decapeptide containing l0 thymine bases in 21% overall yield.
๐ SIMILAR VOLUMES
The first solid-phase synthesis of novel peptide-derived enantiospecific nucleic acid analogs (PDNAs), employing all three stereoisomers of 4-(N 9 -adeninyl)-2-amino(t-boc)-butyric acid as ADNA (amino acid-derived nucleoside analogs) monomers has been described. The preliminary melting temperature (
Boc/'Z-protected PNA oligomers were synthesised on solid phase. The use of the allylic HYCRON resin allowed for the application of both Boc-and Fmoc-protecting groups. Highest yields were obtained when the monomeric building block was synthesised on solid phase rather than loaded as preformed unit.
A convergent and cost-effective strategy to synthesize enantiospecific nucleoside/ nucleotide analogs from readily available อฐ-amino acids has been described. Both (L)-and (D)-methionine were transformed in four steps to the corresponding key intermediates (L)-and (D)-2-(tertbutyloxycarbonylamino)-4