重新评估COMU在不同溶剂中的稳定性。

Re-evaluating the stability of COMU in different solvents.

作者信息

Kumar Ashish, Jad Yahya E, de la Torre Beatriz G, El-Faham Ayman, Albericio Fernando

机构信息

School of Chemistry and Physics, University of KwaZulu-Natal, Durban, 4001, South Africa.

School of Health Sciences, University of KwaZulu-Natal, Durban, 4001, South Africa.

出版信息

J Pept Sci. 2017 Oct;23(10):763-768. doi: 10.1002/psc.3024. Epub 2017 Jul 6.

DOI:10.1002/psc.3024

PMID:28681413

Abstract

COMU is uronium-type coupling reagent based on OxymaPure. It showed several advantages over classical benzotriazole-based coupling reagents such as higher solubility, water-soluble byproduct, and monitoring the reaction by changing of color. Although COMU is well known to perform excellent in solution, but its hydrolytic stability in DMF limits its use in automatic peptide synthesizer. Herein, we evaluated the hydrolytic stability of COMU in γ-valerolactone (GVL), acetonitrile (ACN) and N-formylmorpholine (NFM) and compared its stability against DMF. The stability of COMU after 24 h was found to be 88 and 89% in GVL and ACN, respectively, when compared in DMF (14%). Further, the demanding Aib-ACP decapeptide and JR decapeptide were successfully synthesized using COMU dissolved in GVL or ACN while Fmoc amino acids were dissolved in DMF. Copyright © 2017 European Peptide Society and John Wiley & Sons, Ltd.

摘要

COMU是一种基于OxymaPure的脲鎓型偶联试剂。与传统的基于苯并三唑的偶联试剂相比，它具有几个优点，如更高的溶解度、水溶性副产物以及通过颜色变化监测反应。尽管众所周知COMU在溶液中表现出色，但其在DMF中的水解稳定性限制了它在自动肽合成仪中的应用。在此，我们评估了COMU在γ-戊内酯（GVL）、乙腈（ACN）和N-甲酰吗啉（NFM）中的水解稳定性，并将其稳定性与DMF进行了比较。与DMF（14%）相比，发现COMU在GVL和ACN中24小时后的稳定性分别为88%和89%。此外，使用溶解在GVL或ACN中的COMU成功合成了具有挑战性的Aib-ACP十肽和JR十肽，同时将Fmoc氨基酸溶解在DMF中。版权所有© 2017欧洲肽学会和约翰威立父子有限公司。