Delay of coupling caused by excess additives

✍ Scribed by Sukekatsu Nozaki

• Book ID: 105360507
• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 100 KB
• Volume: 12
• Category: Article
• ISSN: 1075-2617
• DOI: 10.1002/psc.689

✦ Synopsis

Abstract

Use of excess quantity of additives such as 1‐hydroxybenzotriazole, 1‐hydroxy‐7‐azabenzotriazole, or 3,4‐dihydro‐3‐hydroxy‐4‐oxo‐1,2,3‐benzotriazine could retard carbodiimide‐mediated peptide coupling or aminolysis of the active esters in organic solvents generally employed in peptide chemistry. Solubility test and infrared spectroscopic data suggested that the amine components interacted with the additives to form some aggregates, which were less reactive toward acylation. The use of 0.1 equimolar additives against carboxyl components or carbodiimides was advantageous for rapid and efficient coupling reaction, especially when the carboxyl components were amino acids carrying urethane type N‐protecting groups. Copyright © 2005 European Peptide Society and John Wiley & Sons, Ltd.