109337-83-9Relevant academic research and scientific papers
Ecological base-conditioned preparation of dipeptides using unprotected α-amino acids containing hydrophilic side chains
Ezawa, Tetsuya,Jung, Seunghee,Kawashima, Yuya,Noguchi, Takuya,Imai, Nobuyuki
, p. 689 - 696 (2017/07/22)
The coupling reactions of 3-phenylpropanoic acid and Ncarboxybenzyl á-amino acids with unprotected á-amino acids containing hydrophilic side chains such as aliphatic alcohol, aromatic alcohol, thiol, carboxylic acid, and amide afforded the corresponding amides in 6696% yield without racemization via the corresponding mixed carbonic carboxylic anhydrides under basic conditions through an ecological green synthetic method.
Synthesis, molecular docking and anticancer studies of peptides and iso-peptides
Jabeen, Farukh,Panda, Siva S.,Kondratyuk, Tamara P.,Park, Eun-Jung,Pezzuto, John M.,Ihsan-Ul-Haq,Hall, C. Dennis,Katritzky, Alan R.
supporting information, p. 2980 - 2984 (2015/06/22)
Chiral peptides and iso-peptides were synthesized in excellent yield by using benzotriazole mediated solution phase synthesis. Benzotriazole acted both as activating and leaving group, eliminating frequent use of protection and subsequent deprotection. The procedure was based on the hypothesis that epimerization should be suppressed in solution due to a faster coupling rate than SPPS. All the synthesized peptides complied with Lipinski's Ro5 except for the rotatable bonds. Inhibition of cell proliferation of cancer cell lines is one of the most commonly used methods to study the effectiveness of any anticancer agents. Synthesized peptides and iso-peptides were tested against three cancer cell lines (MCF-7, MDA-MB 231) to determine their anti-proliferative potential. NFkB was also determined. Molecular docking studies were also carried out to complement the experimental results.
Chemical ligation from O-acyl isopeptides via 8-and 11-membered cyclic transition states
Panda, Siva S.,Elagawany, Mohamed,Marwani, Hadi M.,Calyakan, Eray,El Khatib, Mirna,Oliferenko, Alexander,Alamry, Khalid A.,Katritzky, Alan R.
, p. 91 - 106 (2014/04/17)
Unprotected O-acylated serine and O-acylated threonine isopeptides have been synthesized, and their conversion to native tripeptides and tetrapeptides by O-to N-terminus transfer investigated. Ligations involving 8-and 11-membered cyclic transition states
Traceless chemical ligations from O-acyl serine sites
El Khatib, Mirna,Elagawany, Mohamed,Jabeen, Farukh,Todadze, Ekaterina,Bol'Shakov, Oleg,Oliferenko, Alexander,Khelashvili, Levan,El-Feky, Said A.,Asiri, Abdullah,Katritzky, Alan R.
supporting information; experimental part, p. 4836 - 4838 (2012/07/28)
Chemical ligation via O- to N-acyl transfer of O-acylated serine containing peptides affords serine containing native peptides via 8- and 11-membered cyclic transition states opening the door to a wide variety of potential applications to peptide elaborat
Highly diastereoselective peptide chain extensions of unprotected amino acids with N-(Z-α-aminoacyl)benzotriazoles
Katritzky, Alan R.,Suzuki, Kazuyuki,Singh, Sandeep K.
, p. 2645 - 2652 (2007/10/03)
Coupling an unprotected amino acid or dipeptide in partially aqueous solution with a readily available N-(Z-α-amino-acyl)benzotriazole or N-(Z-α-aminopetidoyl)benzotriazole affords N-terminal-protected di-, tri-, and tetrapeptides in yields of 85-98% (average 95% for 2a-i, 93% for 4a-f and 4a′, 86% for 5a-b) with minimal epimerization.
Pseudo-prolines as a molecular hinge: Reversible induction of cis amide bonds into peptide backbones
Dumy, Pascal,Keller, Michael,Ryan, Declan E.,Rohwedder, Barbara,W?hr, Torsten,Mutter, Manfred
, p. 918 - 925 (2007/10/03)
Serine, threonine-derived (4S)-oxazolidine-4-carboxylic acid, and cysteine-derived (4R)-thiazolidinecarboxylic acid, denoted pseudo-proline (Xaa[Ψ(R1,R2)pro]), serve as structure disrupting, solubilizing building blocks in peptide sy
A One-Pot Peptide Synthesis via Se-phenyl Carboselenoate in Mixed Aqueous/Organic Solvent System
Ghosh, Sunil Kumar,Singh, Usha,Chandha, Mohindra S.,Mamdapur, Vasant R.
, p. 1566 - 1568 (2007/10/02)
A one pot synthesis of peptides with free C-terminal residues has been accomplished via the active Se-phenyl carboselenoate using diphenyl diselenide, tributylphosphine, and N-methylmorpholine N-oxide in an acetonitrile- water mixed solvent system.Free amino acids and peptides have been used as the amine component without pH adjustment.
Peptide-bond Formation, Chemoselective Acylation of Amino Acids, and Crosslinking Reaction between Amino Acids Utilizing a Functional Five-membered Heterocycle, 1,3-Thiazolidine-2-thione
Nagao, Yoshimitsu,Miyasaka, Tadayo,Seno, Kaoru,Fujita, Eiichi,Shibata, Daisuke,Doi, Etsushiro
, p. 2439 - 2446 (2007/10/02)
The monitored aminolysis of 3-acyl-1,3-thiazolidine-2-thiones has been extended to the peptide-bond formation, the chemoselective acylation of amino acids having multifunctional groups, and the crosslinking reaction between amino acids.
Amino Acids and Peptides. III. Synthesis of Model Peptides Related to Cytochrome P-450
Kawasaki, Koichi,Maeda, Mitsuko,Tamura, Hiromi,Ohashi, Sumiko,Yoshimura, Tetsuhiko,Hatayama Etsuji et al.
, p. 1717 - 1723 (2007/10/02)
Various tetra- and pentapeptides with Cys and Ser (Thr, Tyr, His) at the N- and C-terminals, respectively, were synthetized as model peptides of the apoprotein of cytochrome P-450.The optical spectra of synthetic peptide-hemin complexes were measured and the results are discussed.Keywords - cytochrome P-450; synthetic Cys-containing peptide; peptide-hemin complex; optical spectrum of peptide-hemin complex
