title: Highly efficient and fast pre-activation cyclization of the long peptide: Succinimidyl ester-amine reaction revisited.
abstract: A new method for the pre-activation cyclization of a long peptide is described. The approach involves the formation of a pre-activated succinimidyl ester species in advance of amidation, which completely eliminates the potentially troublesome amine end-capping side reaction. The cyclization reactions proceed with high efficiency and fast reaction kinetics for the long peptide with 25 residues. The exploration and large-scale preparation of synthetic cyclic peptides should become more accessible and feasible with this approach. This method has a potential to be further applied for the synthesis of much longer and more complex cyclic peptides.
authors.affiliation: Translational Research Center for Protein Function Control & Department of Materials Science & Engineering, Yonsei University, Seoul 120-749, Republic of Korea.
authors.forename: Se-Hwan
authors.initials: SH
authors.lastname: Choi
authors.affiliation: Translational Research Center for Protein Function Control & Department of Materials Science & Engineering, Yonsei University, Seoul 120-749, Republic of Korea.
authors.forename: Woo-jin
authors.initials: WJ
authors.lastname: Jeong
authors.affiliation: Translational Research Center for Protein Function Control & Department of Materials Science & Engineering, Yonsei University, Seoul 120-749, Republic of Korea.
authors.forename: Sung-ju
authors.initials: SJ
authors.lastname: Choi
authors.affiliation: Translational Research Center for Protein Function Control & Department of Materials Science & Engineering, Yonsei University, Seoul 120-749, Republic of Korea. Electronic address: yblim@yonsei.ac.kr.
authors.forename: Yong-beom
authors.initials: YB
authors.lastname: Lim
mesh_terms: D000588:Amines / Q000737:chemistry*; D002623:Chemistry Techniques, Analytical; D003500:Cyclization; D010455:Peptides / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000737:chemistry*; D013997:Time Factors
chemical_list: D000588:Amines; D010455:Peptides; D010456:Peptides, Cyclic
keywords: Cyclization; End-capping; Macrocyclic peptides; Pre-activation; Succinimidyl ester