| Title | Influence of alpha-methylation in constructing stapled peptides with olefin metathesis |
| Authors | Zhang, Qingzhou Shi, Xiaodong Jiang, Yanhong Li, Zigang |
| Affiliation | Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Shenzhen 518055, Guangdong, Peoples R China. Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, PKU Campus, Shenzhen 518055, Guangdong, Peoples R China. |
| Keywords | Macro-cyclic peptide alpha-Methylation alpha-Helix Ring-closing metathesis RING-CLOSING METATHESIS HYDROGEN-BOND-SURROGATE AMINO-ACIDS HELIX INHIBITORS DESIGN STABILITY CHAIN |
| Issue Date | 2014 |
| Publisher | tetrahedron |
| Citation | TETRAHEDRON.2014,70,(42),7621-7626. |
| Abstract | Ring-closing metathesis is commonly utilized in peptide macro-cyclization. The influence of alpha-methylation of the amino acids bearing the olefin moieties has never been systematically studied. In this report, controlled reactions unambiguously indicate that alpha-methylation at the N-terminus of the metathesis sites is crucial for this reaction to occur. Also, we first elucidated that the E-isomers of stapled peptides are significantly more helical than the Z-isomers. (C) 2014 Elsevier Ltd. All rights reserved. |
| URI | http://hdl.handle.net/20.500.11897/209928 |
| ISSN | 0040-4020 |
| DOI | 10.1016/j.tet.2014.08.004 |
| Indexed | SCI(E) |
| Appears in Collections: | 化学生物学与生物技术学院 |
