72156-61-7Relevant academic research and scientific papers
NDTP Mediated Direct Rapid Amide and Peptide Synthesis without Epimerization
Li, Yiping,Li, Jingyue,Bao, Guangjun,Yu, Changjun,Liu, Yuyang,He, Zeyuan,Wang, Peng,Ma, Wen,Xie, Junqiu,Sun, Wangsheng,Wang, Rui
supporting information, p. 1169 - 1174 (2022/01/28)
Herein, we explored an unprecedented mild, nonirritating, conveniently available, and recyclable coupling reagent NDTP, which could activate the carboxylic acids via acyl thiocyanide and enable the rapid amide and peptide synthesis at very mild conditions
Photochemical Chemoselective Alkylation of Tryptophan-Containing Peptides
Laroche, Benjamin,Tang, Xinjun,Archer, Gaétan,Di Sanza, Riccardo,Melchiorre, Paolo
supporting information, p. 285 - 289 (2021/01/26)
We report a photochemical method for the chemoselective radical functionalization of tryptophan (Trp)-containing peptides. The method exploits the photoactivity of an electron donor-acceptor complex generated between the tryptophan unit and pyridinium sal
Catalytic enantioselective acyl transfer: the case for 4-PPY with a C-3 carboxamide peptide auxiliary based on synthesis and modelling studies
Cozett, Rudy E.,Venter, Gerhard A.,Gokada, Maheswara Rao,Hunter, Roger
supporting information, p. 10914 - 10925 (2016/12/06)
A series of 4-pyrrolidinopyridine (4-PPY) C-3 carboxamides containing peptide-based side chains have been synthesised and evaluated in the kinetic resolution of a small library of chiral benzylic secondary alcohols. A key design element was the incorporation of a tryptophan residue in the peptide side chain for promoting π-stacking between peptide side chain and the pyridinium ring of the N-acyl intermediate, in which modelling was used as a structure-based guiding tool. Together, a catalyst containing a LeuTrp-N-Boc side chain (catalyst 8) was identified that achieved s-values up to and in slight excess of 10. A transition-state model based on the modelling is proposed to explain the origin of enantioselectivity. This study establishes the usefulness of modelling as a structure-based guiding tool for enantioselectivity optimization as well as the potential for developing scalable peptide-based DMAP-type catalysts for large-scale resolution work.
Cyclic dipeptides exhibit potency for scavenging radicals
Furukawa, Tadashi,Akutagawa, Takashi,Funatani, Hitomi,Uchida, Toshikazu,Hotta, Yoshihiro,Niwa, Masatake,Takaya, Yoshiaki
experimental part, p. 2002 - 2009 (2012/05/04)
Twenty kinds of cyclic dipeptides containing l-leucine were synthesized, and their antioxidant activity against .OH and O2·- was investigated. Compounds possessing polar amino acid residues, such as Asp, Cys, Glu, Lys, Pro, Ser, and Trp, exhibited higher antioxidant activity against .OH than vitamin E. However, only cyclo(l-Cys-l-Leu) scavenged O2·-.
Tryptophan-containing dipeptide derivatives as potent PPARγ antagonists: Design, synthesis, biological evaluation, and molecular modeling
Deng, Guanghui,Liu, Zhiguo,Ye, Fei,Luo, Xiaomin,Zhu, Weiliang,Shen, Xu,Liu, Hong,Jiang, Hualiang
experimental part, p. 2699 - 2716 (2009/04/11)
The discovery of peroxisome proliferator-activated receptor γ (PPARγ) antagonists (also termed "selective PPARγ modulators, SPPARγM") is now of a great interest in the treatment of diabetes and obesity. The structure of compound 1a (G3335, Fig. 1), a novel class of PPARγ antagonist, is entirely different from that of other reported PPARγ antagonists. A series of 35 novel analogues (1b-l, 9a-d, 13a-t) were designed, synthesized and evaluated against the agonistic effects exerted by rosiglitazone. These results indicated that most functional groups of 1a were conserved, and six new compounds (1b, 1c, and 9a-d) exhibited strong PPARγ antagonistic activities (IC50 values of 5.2-25.8 μM) against 10 μM rosiglitazone in the promotion of the PPARγ-LBD-CBP (ligand-binding domain and cAMP-response-element binding protein) interaction as investigated by yeast two-hybrid technology based assay. Molecular modeling studies for compounds 1a-d, 1h, 9c-d, and 13a were also presented.
Selective inhibitors of the serine protease plasmin: Probing the S3 and S3′ subsites using a combinatorial library
Xue, Fengtian,Seto, Christopher T.
, p. 6908 - 6917 (2007/10/03)
A combinatorial library of 400 serine protease inhibitors with the general structure Cbz-Xaa-Trp-cyclohexanone-Trp-Yaa-OH has been constructed. The library was synthesized on the solid phase using mix-and-split synthesis, where 20 di
Polymer-bound triarylphosphine-iodine complexes, convenient coupling reagent systems in peptide synthesis
Caputo,Cassano,Longobardo,Mastroianni,Palumbo
, p. 141 - 143 (2007/10/02)
N-protected α-amino acids are readily coupled with α-aminoacyl esters by polystyryl diphenylphosphine-iodine complex in very high yields and without detectable racemization. Protecting groups of general use for both amine and carboxyl functions, as well a
