156597-80-7Relevant articles and documents
Synthesis of constrained tetracyclic peptides by consecutive CEPS, CLIPS, and oxime ligation
Streefkerk, Dieuwertje E.,Schmidt, Marcel,Ippel, Johannes H.,Hackeng, Tilman M.,Nuijens, Timo,Timmerman, Peter,Van Maarseveen, Jan H.
supporting information, p. 2095 - 2100 (2019/04/11)
In Nature, multicyclic peptides constitute a versatile molecule class with various biological functions. For their pharmaceutical exploitation, chemical methodologies that enable selective consecutive macrocyclizations are required. We disclose a combination of enzymatic macrocyclization, CLIPS alkylation, and oxime ligation to prepare tetracyclic peptides. Five new small molecular scaffolds and differently sized model peptides featuring noncanonical amino acids were synthesized. Enzymatic macrocyclization, followed by one-pot scaffold-assisted cyclizations, yielded 21 tetracyclic peptides in a facile and robust manner.
General and Facile Route to Isomerically Pure Tricyclic Peptides Based on Templated Tandem CLIPS/CuAAC Cyclizations
Richelle, Gaston J. J.,Ori, Sumeet,Hiemstra, Henk,van Maarseveen, Jan H.,Timmerman, Peter
supporting information, p. 501 - 505 (2017/12/26)
We report a one-pot ligation/cyclization technology for the rapid and clean conversion of linear peptides into tricyclic peptides that is based on using tetravalent scaffolds containing two benzyl bromide and two alkyne moieties. These react via CLIPS/CuAAC reactions with cysteines and azides in the peptide. Flexibility in the scaffolds is key to the formation of isomerically pure products as the flexible scaffolds T41 and T42 mostly promote the formation of single isomeric tricycles while the rigid scaffolds T43 and T44 do not yield clean products. There seems to be no limitation to the number and types of amino acids present as 18 canonical amino acids were successfully implemented. We also observed that azides at the peptide termini and cysteine residues in the center gave better results than compounds with the functional groups placed the other way round.
Molecular Tweezers from Cyclophane Building Blocks
Guether, Ralf,Nieger, Martin,Rissanen, Kari,Voegtle, Fritz
, p. 743 - 758 (2007/10/02)
Molecular tweezer compounds 1-6 with convergent carboxyl groups are prepared from suitable functionalized - and dithiametacyclophane building blocks by using several multistep strategies.The C-C coupling of two cyclophanes according to the Hagih