New protective groups for peptide synthesis—II the Dobz group boron-derived affinity protection with the p-dihydroxyborylbenzyloxycarbonylamino function

✍ Scribed by D.S. Kemp; David C. Roberts

• Book ID: 104224173
• Publisher: Elsevier Science
• Year: 1975
• Tongue: French
• Weight: 261 KB
• Volume: 16
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)91037-2

✦ Synopsis

Prutecting groups which permit modification of solubility properties of peptide derivatives or which can act as "handles",1 allowing isolation by selective affinity, offer great potential for facilitating the manipulations of peptide chemistry."2 We report preparation and properties of p-dihydroxyborylbenzyloxycarbonyl (Dobz) amino acid derivatives. As a boronic acid derivative, the Dobz group has very versatile solubilizing and affinity properties. Transformations or manipulations of Dobz derivatives offer the unusual feature that the reactive hydroxyl functions of the boronic acid (pK, % 9) can be masked by rapid, reversible reaction with diols such as catechol, alkyldiethanolamine, or naphthalene-l,B-diol derivatives.