30189-51-6Relevant articles and documents
Enhancement of the small intestinal uptake of phenylalanylglycine via a H+/oligopeptide transport system by chemical modification with fatty acids
Fujita, Takuya,Morishita, Yutaka,Ito, Hitomi,Kuribayashi, Daisuke,Yamamoto, Akira,Muranishi, Shozo
, p. 2455 - 2465 (1997)
The transport characteristics of chemically modified phenylalanylglycine (PheGly) with butyric acid (C4-Phe-Gly) and caproic acid (C6-Phe-Gly) were examined using rabbit intestinal brush-border membrane vesicles (BBMVs). In the prese
Synthesis of fully Protected Peptides on a Tetraethyleneglycol Diacrylate (TTEGDA)-Crosslinked Polystyrene support with a Photolytically Detachable 2-Nitrobenzyl Anchoring group
Renil, M.,Pillai, V. N. Rajasekharan
, p. 3809 - 3812 (1994)
1-Chloromethyl-2-nitro tetraethyleneglycol diacrylate (TTEGDA)-crosslinked polystyrene resin was prepared by nitration of chloromethyl (4percent) TTEGDA-crosslinked polystyrene resin and used as a photosensitive solid support for the preparation of fully
Facile Cu(ii)-mediated conjugation of thioesters and thioacids to peptides and proteins under mild conditions
Sun, Yao,Lyu, Zhenbin,Wang, Zhiqiang,Zeng, Xiaodong,Zhou, Hui,Xu, Fuchun,Chen, Ziyang,Xu, Yuling,Xu, Ping,Hong, Xuechuan
supporting information, p. 3610 - 3614 (2018/05/26)
The bioconjugation of peptide derivatives such as polypeptides, peptide-based probes and proteins is a vibrant area in many scientific fields. However, reports on metal-mediated chemical methods towards native peptides especially non-engineering protein modification under mild conditions are still limited. Herein, we describe a novel Cu(ii)-mediated strategy for the conjugation of thioesters/thioacids to peptides under mild conditions with high functional group tolerance. Based on this strategy, polypeptides, even peptide-based fluorescent probes, can be efficiently constructed. Finally, the selective modification of lysine residues of native Ub with thioesters could be realized and complete conjugation of Ub could be achieved even under equivalent Cu(ii). These promising results could greatly expand Cu(ii)-mediated reaction strategies on chemical biology and molecular imaging.
Synthesis and conformational characterization of diketopiperazines bearing a benzyl moiety
Nakao, Michiyasu,Toriuchi, Yuriko,Fukayama, Shintaro,Sano, Shigeki
, p. 340 - 342 (2014/03/21)
Diketopiperazines bearing a benzyl moiety with different para-substituents were synthesized and analyzed by 1HNMR spectroscopy. All of these diketopiperazines were found to adopt a folded conformation according to the upfield chemical shift of the cis-proton (cis to the benzyl moiety) due to a shielding effect in the 1HNMR spectra. An intramolecular CH-π interaction appears to be an important factor for the folded conformation due to the effects of para-substituents on the benzyl group.
Phosphorus oxychloride as an efficient coupling reagent for the synthesis of esters, amides and peptides under mild conditions
Chen, Hu,Xu, Xunfu,Liu, Liu,Tang, Guo,Zhao, Yufen
, p. 16247 - 16250 (2013/09/23)
A mild method is described for the conversion of carboxylic acids into esters, amides, as well as peptides without racemization through carboxyl activation by the reagent combination of POCl3 and DMAP. Long chain alcohols could be converted to the corresponding ester in good yields. 31P NMR spectrum was used to detect phosphorus-containing intermediates in ongoing reactions directly, and a possible mechanism has been proposed based on these results. The Royal Society of Chemistry 2013.
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.
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.
Synthesis of dipeptides from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione activated α-amino acids
Nowshuddin, Shaik,Ram Reddy
, p. 22 - 25 (2011/04/18)
A simple two step procedure for the synthesis of a dipeptide from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione (HO-ASUD) activated α-amino acids is described. In presence of DCC, N-hydroxy-3-azaspiro[5,5]undecane-2,4- dione readily esterifies the carboxylic acid group of all the N-protected amino acids to yield crystalline N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy ester. The N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy esters of N-protected amino acids readily condensed with other amino acids and gave a dipeptide. This new method is effective for the DCC coupling of a variety of chiral amino acids without loss of enantiomeric purity. Synthesis of fifteen dipeptides including the hitherto unreported Fmoc-l-Orn(Boc)-Val-OMe, Fmoc-l-Cys(trt)-Gly-OEt and Boc-l-Tyr-Gly-OEt is presented.
Stereoselective ring contraction of 2,5-diketopiperazines: An innovative approach to the synthesis of promising bioactive 5-membered scaffolds
Coursindel, Thibault,Restouin, Audrey,Dewynter, Georges,Martinez, Jean,Collette, Yves,Parrot, Isabelle
experimental part, p. 210 - 217 (2010/10/01)
Ring contraction of 2,5-diketopiperazines by TRAL-alkylation led us to the stereoselective synthesis of original pyrrolidine-2,4-diones, a novel series of promising molecules with moderate anti-proliferative activity on breast cancer cells.
Catalytic staudinger-vilarrasa reaction for the direct ligation of carboxylic acids and azides
Bures, Jordi,Martin, Manuel,Urpi, Felix,Vilarrasa, Jaume
experimental part, p. 2203 - 2206 (2009/08/07)
2,2 -Dipyridyl diselenide (PySeSePy) is the catalyst or activator of choice for the direct reaction of carboxylic acids with azides and trimethylphosphine at room temperature. The mechanism of the process, which is not an aza-Wittig reaction, has been elucidated.
