Synthesis of tetrazole analogs of γ- and δ-amino acids

✍ Scribed by Panagiota Moutevelis-Minakakis; Maria Filippakou; Charalambos Sinanoglou; George Kokotos

• Book ID: 105360557
• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 126 KB
• Volume: 12
• Category: Article
• ISSN: 1075-2617
• DOI: 10.1002/psc.737

✦ Synopsis

Abstract

N‐benzyloxycarbonyl‐protected α‐ or β‐amino alcohols, easily prepared from α‐ and β‐amino acids, were converted into aldehydes and directly reacted with (triphenyl phosphoranylidene) acetonitrile, leading to unsaturated nitriles. Treatment of nitriles with NaN~3~ and ZnBr~2~ produced unsaturated γ‐ and δ‐amino tetrazoles, which were deprotected and converted to the corresponding saturated compounds by catalytic hydrogenation. For the case of δ‐amino tetrazole, the methylation of the acidic moiety occurred after treatment with CH~2~N~2~, leading to the N^1^‐ and N^2^‐methylated constitutional isomers, which were separated by column chromatography and hydrogenated. Copyright © 2006 European Peptide Society and John Wiley & Sons, Ltd.