Novel synthesis of α-PNA monomers by U-4CR

• Published in: Amino acids Vol. 34; no. 3; pp. 449 - 453
• Main Authors: Huang, P.-C, Hsu, G.-J, Zhuang, B.-R, Sung, K
• Format: Journal Article
• Language: English
• Published: Vienna Vienna : Springer-Verlag 01.04.2008; Springer-Verlag
• Subjects: Adenines; Amino acids; Analytical Chemistry; Biochemical Engineering; Biochemistry; Biomedical and Life Sciences; Cleavage; Glycine; Life Sciences; Molecular Structure; Monomers; Multi-component reaction; Neurobiology; Peptide; Peptide Nucleic Acids - chemical synthesis; Peptide Nucleic Acids - chemistry; Photochemical; PNA; Proteomics; Synthesis; Keywords: PNA – Multi-component reaction – Peptide
• ISSN: 0939-4451; 1438-2199
• DOI: 10.1007/s00726-007-0548-6

A novel synthesis of α-PNA monomers was carried out by U-4CR, followed by photochemical cleavage of the 2-nitrobenzyl group and selective hydrolysis in the presence of 10% HCl in THF. Three of four functional components in the U-4CR were specially protected: cyclohexenyl isocyanide, Boc for protecting the amino group of glycine, and 2-nitrobenzyl group as a photocage (photoremovable protecting group) for ammonia. The amino group of aldehyde-containing adenine is too weak to interfere with the U-4CR, so that it is not necessary to be protected.