2766-31-6Relevant academic research and scientific papers
Tandem deprotection/coupling for peptide synthesis in water at room temperature
Cortes-Clerget, Margery,Berthon, Jean-Yves,Krolikiewicz-Renimel, Isabelle,Chaisemartin, Laurent,Lipshutz, Bruce H.
supporting information, p. 4263 - 4267 (2017/09/28)
A tandem deprotection/coupling sequence is reported for solution-phase peptide synthesis in water under micellar catalysis conditions using the designer surfactant TPGS-750-M. Cbz deprotection followed by peptide coupling in the presence of COMU and 2,6-lutidine afforded polypeptides containing up to 10 amino acid residues. A broad scope characterizes this new technology. No epimerization has been detected. The associated E Factors, as a measure of "greenness" and known to be extremely high for peptide couplings, have been reduced to less than 10 due to the step-economy and minimal amounts of organic solvent needed for product extraction.
Borinic acid catalysed peptide synthesis
El Dine, Tharwat Mohy,Rouden, Jacques,Blanchet, Jér?me
supporting information, p. 16084 - 16087 (2015/11/10)
The catalytic synthesis of peptides is a major challenge in the modern organic chemistry hindered by the well-established use of stoichiometric coupling reagents. Herein, we describe for the first time that borinic acid is able to catalyse this reaction under mild conditions with an improved activity compared to our recently developed thiophene-based boronic acid. This catalyst is particularly efficient for peptide bond synthesis affording dipeptides in good yields without detectable racemization.
An efficient protocol for the amidation of carboxylic acids promoted by trimethyl phosphite and iodine
Luo, Qun-Li,Lv, Lina,Li, Yu,Tan, Jian-Ping,Nan, Wenhui,Hui, Qun
supporting information; experimental part, p. 6916 - 6922 (2012/01/06)
A practical, one-pot protocol is described for the conversion of carboxylic acids into amides through carboxyl activation by the reagent combination of trimethyl phosphite and iodine. This method integrates several advantages: (1) it allows amines to be chemoselectively acylated with excellent results in the presence of sulfur and oxygen nucleophiles; (2) the method shows wide generality in respect of solvent, base, and substrate; (3) the reagents used are widely available and much less expensive than common coupling reagents, and (4) the process is remarkably convenient, permitting extraction, recrystallization, and column chromatography as optional work-up procedures. The chemoselectivity and generality of the method, the low cost, and wide availability of reagents combined with the ease of use make it a very favorable process.
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
, 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
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.
New Carbodiimides for Peptide Synthesis
Orlowska, A.,Izdebski, J.
, p. 713 - 718 (2007/10/02)
Three carbodiimides: N,N'-dicyclopentylcarbodiimide, N,N'-di-2-methylcyclohexylcarbodiimide and N,N'-dimenthylcarbodiimide were prepared and used for activation of the carboxyl group in peptide coupling reactions.Several model reactions were carried out t
KINETICS OF THE ALKALINE HYDROLYSIS OF SEVERAL N-BENZYLOXYCARBONYLDIPEPTIDE METHYL AND ETHYL ESTERS
Hoogwater, D. A.,Peereboom, M.
, p. 5325 - 5332 (2007/10/02)
The reaction rates of the alkaline hydrolysis of synthesized N-protected dipeptide methyl and ethyl esters were studied systematically.From the kinetic data the energies of activation, the pre-exponential factors and the reference values at 40 deg C were calculated.The rate of hydrolysis shows to be strongly dependent on the C-terminal amino acid in the sequence Gly >> Ala/Met/Phe > Leu >> Val/Pro.Surprisingly the N-terminal amino acid also exerts an effect, but in a different sequence.N-Terminal Phe in particular shows a relative accelerating effect.Remarkable is the significantly faster ester hydrolysis of glycine containing dipeptide ethyl esters in ethanol/water compared to the corresponding methyl esters in methanol/water.
