Design and synthesis of rhamnose-modified exenatide conjugate by sortase A-mediated ligation. Issue 3 (24th March 2019)

• Record Type: Journal Article
• Authors: Li, Chen; Dai, Shijie; Cao, Aijie; Zhou, Zhifang; Wu, Zhimeng
• Is Part Of: Journal of carbohydrate chemistry. Volume 38:Issue 3(2019)
• Page Start: 167
• Page End: 178
• Publication Date: 2019-03-24
• Subjects: Exenatide -- sortase A -- rhamnose -- conjugate; Carbohydrates -- Periodicals; 547.78
• DOI: 10.1080/07328303.2019.1609021
• Languages: English
• ISSNs: 0732-8303

Abstract

Abstract: Exenatide modified with rhamnose as a hapten was designed and synthesized by Sortase A-mediated ligation. An Exenatide peptide analog comprised of 46 amino acids, including the sortase A recognition motif LPETG at the C-terminus, was synthesized by solid phase peptide synthesis method. A tri-glycine modified-rhamnose derivative was chemically synthesized in seven steps in good yield. The site-specific conjugation between them catalyzed by Sortase A completed in 3 h and the rhamnose-modified Exenatide conjugate was obtained after semi-preparative HPLC purification and characterized by MALDI-TOF MS. This method should be generally useful for the synthesis of other Exenatide analog for biological studies. Graphical Abstract: