28635-78-1Relevant articles and documents
Peptide Bond Formation of Amino Acids by Transient Masking with Silylating Reagents
Muramatsu, Wataru,Yamamoto, Hisashi
supporting information, p. 6792 - 6797 (2021/05/29)
A one-pot peptide bond-forming reaction has been developed using unprotected amino acids and peptides. Two different silylating reagents, HSi[OCH(CF3)2]3 and MTBSTFA, are instrumental for the successful implementation of this approach, being used for the activation and transient masking of unprotected amino acids and peptides at C-termini and N-termini, respectively. Furthermore, CsF and imidazole are used as catalysts, activating HSi[OCH(CF3)2]3 and also accelerating chemoselective silylation. This method is versatile as it tolerates side chains that bear a range of functional groups, while providing up to >99% yields of corresponding peptides without any racemization or polymerization.
Stereocontrolled [11C]Alkylation of N-Terminal Glycine Schiff Bases To Obtain Dipeptides
Filp, Ulrike,Peko?ak, Aleksandra,Poot, Alex J.,Windhorst, Albert D.
, p. 5592 - 5596 (2017/10/13)
The use of various quaternary ammonium salts as chiral phase-transfer catalysts allowed effective and stereoselective radiochemical [11C]alkylation to obtain functionalized dipeptides. We herein report a broadly applicable procedure for the asymmetric [11C]alkylation of dipeptides to give labeled N-terminal peptides by using different [11C]alkyl halides. Contended stereoselectivities of the reactions were observed by using 11C-labeled alkyl halides, [11C]methyl iodide and [11C]benzyl iodide, and diastereomeric ratios with different specialized catalysts of 95:5 and 90:10 were achieved, respectively. Accordingly, the straightforward synthesis of enantioenriched compounds should play a vital role in peptide-based radiopharmaceutical development and positron emission tomography imaging.
Synthesis of IB-01212 by multiple N-methylations of peptide bonds
Nabika, Ryota,Oishi, Shinya,Misu, Ryosuke,Ohno, Hiroaki,Fujii, Nobutaka
supporting information, p. 6156 - 6162 (2015/01/09)
There are many natural peptides with multiple N-methylamino acids that exhibit potent attractive biological activities. N-methylation of a peptide bond(s) is also one of the standard approaches in medicinal chemistry of bioactive peptides, to improve the