2867-06-3Relevant articles and documents
Facile and purification free synthesis of peptides utilizing ROMPgel- and ROMPsphere-supported coupling reagents
Barrett, Anthony G.M.,Bibal, Brigitte,Hopkins, Brian T.,K?bberling, Johannes,Love, Andrew C.,Tedeschi, Livio
, p. 12033 - 12041 (2005)
5-Norbornene-2-carboxaldehyde and norbornadiene were respectively converted into norbornene derivatives functionalized with fluoroformamidinium hexafluorophosphate and 2-bromo-N-methylpyridinium tetrafluoroborate residues. Both these norbornene monomers were ring opening metathesis polymerized or graft copolymerized onto polystyrene cores to produce ROMPgel and ROMPsphere peptide-coupling reagents. These were used to prepare hindered amides, dipeptides and tripeptides with minimal purification in parallel arrays.
Asymmetric alcoholysis of 2-phenyl-5(4H)-oxazolones by the catalytic mixture of cyclo[(S)-His-(S)-Phe] with chiral auxiliaries
Xie, Lunjia,Hua, Wenting,Chan, Albert S. C.,Leung, Yun-Chang
, p. 4715 - 4728 (1999)
Some derivatives of dipeptides containing a His residue catalyzed the ring opening of 2-phenyl-4-benzyl-5(4H)-oxazolone by methanol. The mixture of cyclo[(S)-His-(S)-Phe] (CHP) with chiral auxiliaries which possess both a hydrogen-bond donor and a hydroge
Organophosphorus esters of 1-hydroxy-2-phenylbenzimidazole: Synthesis and utilization as novel peptide coupling reagents
Kokare, Nagnnath D.,Nagawade, Rahul R.,Rane, Vipul P.,Shinde, Devanand B.
, p. 766 - 772 (2008/01/04)
Highly efficient coupling reagents - phosphoric acid diethyl ester 2-phenylbenzimidazol-1-yl ester, diphenylphosphinic acid 2-phenylbenzimidazol-1- yl ester and phosphoric acid diphenyl ester 2-phenylbenzimidazol-1-yl ester - were designed, synthesized and successfully applied in peptide coupling reactions. Their efficiency was evaluated through the synthesis of a range of amides and peptides, and the extent of racemization was studied by HPLC and found to be negligible. The mechanism of action is probably similar to those found for organophoshorus esters of hydroxybenzotriazole: a presumption supported by the isolation and characterization by mass spectrometry and 1H NMR of some of the proposed intermediates. Georg Thieme Verlag Stuttgart.
A new method for the synthesis of carboxamides and peptides using 1,1′-carbonyldioxydi[2(1H)-pyridone] (CDOP) in the absence of basic promoters
Shiina, Isamu,Kawakita, Yo-Ichi
, p. 1951 - 1955 (2007/10/03)
Various carboxamides or peptides are synthesized from the corresponding carboxylic acids and amines or α-amino acids using 1,1′-carbonyldioxydi[2(1H)-pyridone]. The reaction proceeds in the absence of basic promoters such as triethylamine or 4-(dimethylamino)pyridine, therefore, the undesired racemization does not occur at all in the segment coupling producing Z-Gly-Phe-Val-OMe and Z-Phe-Val-Ala-OMe.