860-55-9Relevant 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
Convenient peptide synthesis using unprotected α-amino acids containing another hydrophilic moiety under basic conditions
Noguchi, Takuya,Jung, Seunghee,Imai, Nobuyuki
scheme or table, p. 577 - 579 (2012/08/08)
Carboxylic acids 1 and 7 reacted effectively with unprotected α-amino acids 2 containing another hydrophilic moiety under basic conditions via activation by ethyl chloroformate and triethylamine to afford the corresponding amides in 7499% yields.
Solid-phase synthesis of 1,3-azole-based peptides and peptidomimetics
Biron, Eric,Chatterjee, Jayanta,Kessler, Horst
, p. 2417 - 2420 (2007/10/03)
We report highly efficient two-step procedures for the synthesis of 1,3-oxazole-, thiazole-, and imidazole-containing peptides on solid phase from dipeptides composed of C-terminal threonine, serine, cysteine, or diaminopropionic acid by using different cyclodehydration procedures followed or preceded by oxidation. The methods are compatible with Fmoc solid-phase peptide synthesis conditions and with N-Fmoc, N-Boc, N-Cbz, and N-Alloc protecting groups.
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.
Peptide coupling of unprotected amino acids through in situ p-nitrophenyl ester formation
Gagnon, Paul,Huang, Xicai,Therrien, Eric,Keillor, Jeffrey W.
, p. 7717 - 7719 (2007/10/03)
Several series of dipeptides and tripeptides were prepared via an activation-coupling method involving the in situ formation of a p-nitrophenyl ester of an (N-protected) amino acid, followed by coupling with an unprotected amino acid in partially aqueous solutions. The resulting peptide is easily isolated by precipitation. In general, the yields obtained are good to excellent and racemization is minimal. This method is particularly advantageous with respect to its simplicity and lack of obligatory side chain protection/deprotection steps.
Selective Enzymatic Removal of Protecting Groups: n-Heptyl Esters as Carboxy Protecting Functions in Peptide Synthesis
Braun, Peter,Waldmann, Herbert,Vogt, Walter,Kunz, Horst
, p. 165 - 170 (2007/10/02)
Amino acid heptyl (Hep) esters are accessible as generally crystalline hydro tosylates 3 from the amino acids by azeotropic esterification with 1-heptanol in high yields.They can be condensed with Z-, Boc-, and Aloc-protected amino acids to give the dipep
SOLUTION SYNTHESIS OF THE HEPTADECAPEPTIDE SEQUENCE OF VESPULAKININ 1
Biondi, Laura,Cavaggion, Franco,Filira, Fernando,Rocchi, Raniero
, p. 427 - 434 (2007/10/02)
Solution synthesis is described of the carbohydrate-free heptadecapeptide sequence of vespulakinin 1.The segment condensation strategy has been utilized to assemble the complete sequence.Carboxyl activation has been achieved by the 1-succinimidyl esters m
