122237-12-1Relevant articles and documents
Effect of Stereochemistry on Chirality and Gelation Properties of Supramolecular Self-Assemblies
Qin, Minggao,Zhang, Yaqian,Xing, Chao,Yang, Li,Zhao, Changli,Dou, Xiaoqiu,Feng, Chuanliang
, p. 3119 - 3129 (2021/01/20)
Although chiral nanostructures have been fabricated at various structural levels, the transfer and amplification of chirality from molecules to supramolecular self-assemblies are still puzzling, especially for heterochiral molecules. Herein, four series o
Deprotection/reprotection of the amino group in α-amino acids and peptides. A one-pot procedure in [Bmim][BF4] ionic liquid
Di Gioia,Barattucci,Bonaccorsi,Leggio,Minuti,Romio,Temperini,Siciliano
, p. 2678 - 2686 (2014/01/06)
This paper presents an efficient one-pot protocol for the sequential deprotection/reprotection of the α-amino group in α-amino acid and dipeptide methyl esters. [Bmim][BF4] is used as the solvent in the entire process. In particular, the use of the ionic liquid allows for rapid and clean removal of the 4-nitrobenzenesulfonyl (nosyl) group and for facile subsequent tert-butyloxycarbonylation of the free α-amino function under very mild conditions. N-Boc-α-amino acid as well as peptide derivatives are isolated in excellent yields, and do not require any further purification. Absolute configurations of the precursors are totally preserved during the process.
Amine capture strategy for peptide bond formation by means of quinolinium thioester salts
Leleu, Stephane,Penhoat, Mael,Bouet, Alexis,Dupas, Georges,Papamicael, Cyril,Marsais, Francis,Levacher, Vincent
, p. 15668 - 15669 (2007/10/03)
A new and unprecedented exploitation of quinolinium thioester salts 2 in peptide bond formation is reported. These synthetic tools were assessed during the preparation of a number of dipeptides 3a-f obtained in good yields with complete stereochemical integrity. A sequential mechanism related to a prior amine capture strategy is well-established. Additionally, a tripeptide 3g was prepared according to a "safety-catch" approach, thus demonstrating the important potential of these new synthetic tools in the design of new safety-catch linkers exploitable in Solid-Phase Peptide Synthesis (SPPS). Copyright