2778-34-9Relevant academic research and scientific papers
Solar and Visible Light Assisted Peptide Coupling
Mishra, Abhaya K.,Parvari, Galit,Santra, Sourav K.,Bazylevich, Andrii,Dorfman, Ortal,Rahamim, Jonatan,Eichen, Yoav,Szpilman, Alex M.
supporting information, p. 12406 - 12412 (2021/04/05)
Amino acid and peptide couplings are widely used in fields related to pharma and materials. Still, current peptide synthesis continues to rely on the use of expensive, water sensitive, and waste-generating coupling reagents, which are often prepared in mu
Scandium(III) triflate-promoted serine/threonine-selective peptide bond cleavage
Ni, Jizhi,Sohma, Youhei,Kanai, Motomu
supporting information, p. 3311 - 3314 (2017/03/22)
The site-selective cleavage of peptide bonds is an important chemical modification that is useful not only for the structural determination of peptides, but also as an artificial modulator of peptide/protein function and properties. Here we report site-selective hydrolysis of peptide bonds at the Ser and Thr positions with a high conversion yield. This chemical cleavage relies on Sc(iii)-promoted N,O-acyl rearrangement and subsequent hydrolysis. The method is applicable to a broad scope of polypeptides with various functional groups, including a post-translationally modified peptide that is unsuitable for enzymatic hydrolysis. The system was further extended to site-selective cleavage of a native protein, Aβ1-42, which is closely related to the onset of Alzheimer's disease.
Phosphine-based redox catalysis in the direct traceless staudinger ligation of carboxylic acids and azides
Kosal, Andrew D.,Wilson, Erin E.,Ashfeld, Brandon L.
supporting information, p. 12036 - 12040 (2013/01/16)
Redox catalysis: Aryl amides, imides, lactams, and dipeptides are obtained through a direct Staudinger ligation mediated by phosphine-based redox catalysis (see scheme). Mechanistic studies indicate the involvement of a phosphonium carboxylate intermediate that leads to a 1,3-acyl migration and thus results in C-N bond formation. Copyright
Metal-free direct amidation of peptidyl thiol esters with α-amino acid esters
Chen, Hao,He, Maomao,Wang, Yaya,Zhai, Linhui,Cui, Yongbo,Li, Yangyan,Lee, Yan,Zhou, Haibing,Hong, Xuechuan,Deng, Zixin
supporting information; experimental part, p. 2723 - 2726 (2011/11/06)
Metal-free direct amidation of peptidyl thiol esters with α-amino acid esters in the presence of bis(trimethylsilyl) acetamide (BSA) has been developed. This general method provides convenient access to N-protected peptides in good yields under mild condi
Design, synthesis, and application of enantioselective coupling reagent with a traceless chiral auxiliary
Kolesinska, Beata,Kaminski, Zbigniew J.
supporting information; experimental part, p. 765 - 768 (2009/09/06)
(Chemical Equation Presented) Stable chiral N-triazinylbrucinium tetrafluoroborate enantioselectively activates racemic carboxylic acids yielding enantiomerically enriched amides, esters, and dipeptides with er from 8:92 to 0.5:99.5. Due to the departure
A flow reactor process for the synthesis of peptides utilizing immobilized reagents, scavengers and catch and release protocols
Baxendale, Ian R.,Ley, Steven V.,Smith, Christopher D.,Tranmer, Geoffrey K.
, p. 4835 - 4837 (2007/10/03)
A general flow process for the multi-step assembly of peptides has been developed and this procedure has been used to successfully construct a series of Boc, Cbz and Fmoc N-protected dipeptides in excellent yields and purities, including an extension of t
Microwave accelerated high speed solution synthesis of peptides employing HATU/HOAt
Sudarshan, Naremaddepalli S.,Suresh Babu, Vommina V.
, p. 1509 - 1511 (2007/10/03)
The chemical synthesis of peptides employing HATU/HOAt as a coupling agent under microwave irradiation has been described. The couplings found to be complete in 30-40 s. The yield as well as purity of the peptides made is found to be good. All the peptide
Ethyl propiolate: A simple and convenient peptide coupling reagent
Iorga, Bogdan,Campagne, Jean-Marc
, p. 1826 - 1828 (2007/10/03)
Ethyl propiolate has been used to activate N-protected amino acids to form a moderately activated vinyl-ester which aminolysis requires a catalytic amount of sodium bisulfite.
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.
A convenient method for the preparations of carboxamides and peptides by using di(2-pyridyl) carbonate and O,O′-di(2-pyridyl) thiocarbonate as dehydrating reagents
Shiina,Suenaga,Nakano,Mukaiyama
, p. 2811 - 2818 (2007/10/03)
Preparations of carboxamides and peptides are performed in high yields from free carboxylic acids and amines by dehydration condensation using di(2-Pyridyl) carbonate (DPC) or O,O′-Di(2-Pyridyl) thiocarbonate (DPTC) in the presence of a catalytic amount of 4-(dimethylamino)pyridine (DMAP). The formation of 2-Pyridyl esters, key intermediates of the reaction, from carboxylic acids by using DPC proceeded faster than by using DPTC; therefore, the former carbonate is more efficiently employed in the above condensation reactions.
