2873-37-2Relevant academic research and scientific papers
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.
HMDO-promoted peptide and protein synthesis in ionic liquids
Duan, Jianli,Sun, Yao,Chen, Hao,Qiu, Guofu,Zhou, Haibing,Tang, Ting,Deng, Zixin,Hong, Xuechuan
, p. 7013 - 7022 (2013/08/23)
Hexamethyldisiloxane (HMDO) has been developed to efficiently promote the metal-free direct coupling of an amino function of one cysteine-free peptide or protein and a C-terminal thioester of the second peptide in ionic liquids. The amide-coupling reaction proceeds smoothly under mild conditions to afford the corresponding products in good to excellent yields (63-94%). Peptide couplings were also achieved using in-situ-generated thioesters by the thioesterification of oxo esters.
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
Dynamic combinatorial libraries of hydrazone-linked pseudo-peptides: Dependence of diversity on building block structure and chirality
Liu, Jingyuan,West, Kevin R.,Bondy, Chantelle R.,Sanders, Jeremy K. M.
, p. 778 - 786 (2008/03/14)
Expanding on our earlier building block architecture [(MeO) 2CH-Linker-Pro-X-NHNH2 where X = Phe, Cha], we have produced a series of new pseudo-dipeptides [(MeO)2CH-Linker-Pro-X- NHNH2 where X = Val, Leu, Ile, A
Small peptides catalyze highly enantioselective direct aldol reactions of aldehydes with hydroxyacetone: Unprecedented regiocontrol in aqueous media
Tang, Zhuo,Yang, Zhi-Hua,Cun, Lin-Feng,Gong, Liu-Zhu,Mi, Ai-Qiao,Jiang, Yao-Zhong
, p. 2285 - 2287 (2007/10/03)
L-Proline-based small peptides have been developed as efficient catalysts for the asymmetric direct aldol reactions of hydroxyacetone with aldehydes. Chiral 1,4-diols 7, which are disfavored products in similar aldol reactions catalyzed by either aldolases or t-proline, were obtained in high yields and enantioselectivities of up to 96% ee with peptides 3 and 4 in aqueous media.
Brush-Border-Enzyme-Mediated Intestine-Specific Drug Delivery. Amino Acid Prodrugs of 5-Aminosalicylic Acid
Pellicciari, Roberto,Garzon-Aburbeh, Aaron,Natalini, Benedetto,Marinozzi, Maura,Clerici, Carlo,et al.
, p. 4201 - 4207 (2007/10/02)
5-Aminosalicylic acid (5-ASA) is the active principle of a number of preparations aimed at the treatment of inflammatory bowel diseases, such as Crohn's disease and ulcerative colitis, but its efficacy is limited by early absorption and metabolism.The pos
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.
PEPTIDE SYNTHESIS BY USING N-ACYLPHOSPHORAMIDITES
Kawanobe, Wataru,Yamaguchi, Kazuo,Nakahama, Seiichi,Yamazaki, Noboru
, p. 825 - 828 (2007/10/02)
New trivalent phosphorus compounds, N-acetyl-N-methylphosphoramidites were prepared readily in good yield by the reaction of phosphorous chlorides and N-methylacetamide.By using the phosphoramidites as condensing agents, Young's peptide and prolyl-leucyl-
