1999-88-8Relevant academic research and scientific papers
A Sterically Overcrowded, Isopropyl-Substituted, Lanthanide-Chelating Tag for Protein Pseudocontact Shift NMR Spectroscopy: Synthesis of its Macrocyclic Scaffold and Benchmarking on Ubiquitin S57 C and hCA II S166 C
Joss, Daniel,Bertrams, Maria-Sophie,H?ussinger, Daniel
supporting information, p. 11910 - 11917 (2019/08/20)
A sterically overcrowded lanthanide-chelating tag has been synthesized in order to investigate the influence on the obtained pseudocontact shifts and the anisotropic part of the magnetic susceptibility tensor compared to those of its predecessor DOTA-M8-(
Sulfonate esters of 1-hydroxypyridin-2(1H)-one and ethyl 2-cyano-2-(hydroxyimino)acetate (Oxyma) as effective peptide coupling reagents to replace 1-hydroxybenzotriazole and 1-hydroxy-7-azabenzotriazole
Khattab, Sherine Nabil
experimental part, p. 501 - 506 (2010/09/06)
A new family of sulfonate ester-type coupling reagents is described which differs in its leaving group. The sulfonate ester coupling reagents ethyl 2-cyano-2-(naphthalen-2-ylsulfonyloxyimino)acetate (NpsOXY), and ethyl 2-cyano-2-(tosyloxyimino)acetate (Ts
Ethyl 2-Cyano-2-(hydroxyimino)acetate (Oxyma): An efficient and convenient additive used with tetramethylfluoroformamidinium hexafluorophosphate (TFFH) to replace 1-hydroxybenzotriazole (HOBt) and 1-hydroxy-7-azabenzotriazole (HOAt) during peptide synthesis
Khattab, Sherine N.
experimental part, p. 1374 - 1379 (2011/02/23)
The appropriateness of ethyl 2-cyano-2-(hydroxyimino)acetate (Oxyma) as a substitute for benzotriazole-based additives, for use in the TFFH approach for peptide synthesis, is discussed in terms of its capacity to control racemization, its coupling efficiency in difficult couplings either for stepwise or segment coupling in solution- and solid-phase coupling. In addition, Boc-based solution-phase peptide synthesis and its stability in the presence of growing peptide chains were studied. Oxyma displayed remarkable results in terms of racemization depression together with impressive coupling efficiency in both solution- and solid-phase synthesis. Furthermore, Oxyma suggests a lower risk of explosion than HOBt and HOAt.
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.
An improved aldehyde linker for the solid phase synthesis of hindered amides
Liley, Mark J.,Johnson, Tony,Gibson, Susan E.
, p. 1322 - 1329 (2007/10/03)
A novel aldehyde dual-linker system has been developed for the solid phase synthesis of sterically hindered amides. The linker [5-(4-formyl-3- hydroxyphenoxy)pentanoic acid] exploits an intramolecular oxygen-nitrogen acyl transfer mechanism to prepare com
Synthesis, solution structure and biological activity of Val-Val-Pro-Gln, a bioactive elastin peptide
Spezzacatena, Caterina,Pepe, Antonietta,Green, Lora M.,Sandberg, Lawrence B.,Bochicchio, Brigida,Tamburro, Antonio M.
, p. 1644 - 1651 (2007/10/03)
Val-Val-Pro-Gln (valyl-valyl-prolyl-glutamine) is a small but highly conserved sequence present in all elastins. We describe its synthesis by mixed anhydride solution chemistry as an alternative to solid-phase peptide synthesis (SPPS). The molecular struc
N, N′-Carbonyldisaccharin: A new condensing agent for the synthesis of amides, esters and peptides
Yadav,Dubey, Suman,Singh, Amrish
, p. 2601 - 2603 (2007/10/03)
A new, easy to handle and efficient condensing agent N,-N′ -carbonyldisaccharin 2 has been readily synthesised by the reaction of saccharin 1 and trichloromethyl chloroformate in toluene. The condensing agent 2 is demonstrated to be useful for the synthesis of amides, esters and dipeptides under mild conditions in a one-pot procedure.
Copper-catalyzed enantioselective conjugate addition of dialkylzinc reagents to enones with new peptidyl phosphane ligands
Breit, Bernhard,Laungani, Andy Ch.
, p. 3823 - 3826 (2007/10/03)
Copper catalysts based on new peptidyl phosphane ligands have been developed for enantioselective conjugate additions of dialkylzinc reagents to cyclic enones. Enantioselectivities greater than 97% ee have been observed.
2-Mercaptopyridine-1-oxide-based peptide coupling reagents
Albericio, Fernando,Bailén, Miguel A,Chinchilla, Rafael,Dodsworth, David J,Nájera, Carmen
, p. 9607 - 9613 (2007/10/03)
The thiouronium salts S-(1-oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium hexafluorophosphate (HOTT) and tetrafluoroborate (TOTT), and S-(1-oxido-2-pyridinyl)-1,3-dimethyl-1,3-trimethylenethiouronium hexafluorophosphate (HODT) and tetrafluoroborate (TODT), prepared from 2-mercaptopyridine-1-oxide and 1,1,3,3-tetramethylurea (TMU) or 1,3-dimethylpropyleneurea (DMPU), have been employed as reagents in solution and solid-phase peptide coupling chemistry. Furthermore, 2-mercaptopyridine-1-oxide has been employed as racemization-reducing additive combined with the new thiouronium salts and other frequently used peptide coupling reagents such as DCC or TBTU.
