32159-21-0Relevant articles and documents
Selective Electrochemical Oxidation of Functionalized Pyrrolidines
Deprez, Nicholas R.,Clausen, Dane J.,Yan, Jia-Xuan,Peng, Feng,Zhang, Shaoguang,Kong, Jongrock,Bai, Yanguang
supporting information, p. 8834 - 8837 (2021/11/20)
A method for the selective electrochemical aminoxyl-mediated Shono-type oxidation of pyrrolidines to pyrrolidinones is described. These transformations show the high selectivity and functional group compatibility. This chemistry also demonstrates the use of an operationally simple ElectraSyn 2.0 and cost-effective stainless-steel electrode for the electrochemical oxidation of functionalized pyrrolidines.
Preparation method of (S)-1 - (benzyloxycarbonyl) -5 -oxo-pyrrolidine -2 - formic acid
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Paragraph 0014; 0017-0018; 0021-0022; 0025-0026; 0029-00..., (2021/09/01)
The invention discloses a preparation method of (S)-1 - (benzyloxycarbonyl) -5 -oxo-pyrrolidine -2 - formic acid, which mainly solves the complexity in the original process, and is long in period and high in cost. The method specifically comprises first steps of preparing L - benzyloxycarbonyl N - glutamic acid from - L - glutamic acid and a benzyloxycarbonyl donor, second steps of intramolecular condensation cyclization N - benzyloxycarbonyl - L - glutamic acid to obtain the N -benzyloxycarbonyl - L - glutamic acid crude product. The third The crude N - benzyloxycarbonyl - L - glutamic acid crude product and the organic amine base are mixed, and the organic amine salt form is prepared by the solubility of the product in a solvent, fourth (N -) - L - (benzyloxycarbonyl) S oxopyrrolidine -1 - formic acid is prepared by desalinating -5 - benzyloxycarbonyl -2 - glutamic acid. To the method, the high-purity product is prepared, and the yield and the quality are greatly improved.
Regioselective opening of N-Cbz glutamic and aspartic anhydrides with carbon nucleophiles
Deguest, Geoffrey,Bischoff, Laurent,Fruit, Corinne,Marsais, Francis
, p. 2120 - 2125 (2007/10/03)
Depending on the experimental conditions, aspartic and glutamic anhydrides can be opened regioselectively with Grignard reagents, thus giving access to different isomers of chiral amino-ketoesters.
Semi-synthetic alanyl didemnin analogs
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, (2008/06/13)
The didemnin class of biologically active cyclodepsipeptides, isolated from the marine tunicate Trididemnun solidum, has shown considerable antitumor, antiviral, and immunosuppressive activities. Didemnin B (DB) and most other natural didemnins contain a common macrocycle and differ only in the composition of the side chain. In the present invention, structural modifications were introduced in the side chain to afford several didemnin analogues for structure-activity relationship studies. The latter have shown that the linear side chain portion of the didemnin core structure can be altered and, in some cases, provide significant gains in bioactivities. Of the compounds synthesized the new [Ala9] didemnin B is the most active against the L1210 (murine leukemia) cell line, at the 0.04 ng/mL level.
Synthesis, characterization and in vitro hydrolysis of L-pyroglutamyl-L-tryptophan derivatives as potential drug carriers
Bousquet,De Regis,Giannola,Santagati,Tirendi
, p. 260 - 262 (2007/10/02)
The condensation reaction of L-tryptophan with L-pyroglutamic acid or its N-carbobenzyloxy derivative in the presence of dicyclohexylcarbodiimide (DCC) afforded dipeptide molecules identified as L-pyroglutamyl-L-tryptophan derivatives. The synthesized dipeptide molecules offer a potentially useful means to obtain drug carriers and improve the poor uptake of drug molecules to the brain. The chemical hydrolysis characteristics in simulated gastro-intestinal juices are reported. No significant hydrolysis was observed.
Synthesis and Siderophore Activity of Albomycin-like Peptides Derived from N5-Acetyl-N5-hydroxy-L-ornithine
Dolence, E. Kurt,Lin, Chia-En,Miller, Marvin J.,Payne, Shelley M.
, p. 956 - 968 (2007/10/02)
N5-Acetyl-N5-hydroxy-L-ornithine (1), the key constituent of several microbial siderophores, has been synthesized in 23percent yield overall from N-Cbz-L-glutamic acid 1-tert-butyl ester (6) derived from L-glutamic acid.Reduction of 6 to 7 and treatment with N-(trichloroethoxy)carbonyl>-O-benzylhydroxylamine (8), and diethyl azodicarboxylate and triphenylphosphine followed by deprotection produced the protected N5-acetyl-N5-hydroxy-L-ornithine derivatives 11 and 12 in large quantities (10-20 g).Following α-amino and α-carboxyl deprotections of 11 and 12, EEDQ mediated peptide coupling and final deprotection provided amino acid 1 and six albomycin-like peptides (20, 23, 25, 28, 35, and 36).The growth-promoting ability of each was evaluated with the siderophore biosynthesis mutant Shigella flexneri SA240 (SA 100 iucD:Tn5).These results indicate that substantial modification of the framework of peptide-based siderophores can be tolerated by microbial iron-transport systems.
Amino Acid Synthesis Using (L)-Pyroglutamic Acid as a Chiral Starting Material
Baldwin, Jack E.,Miranda, Tania,Moloney, Mark,Hokelek, Tuncer
, p. 7459 - 7468 (2007/10/02)
Deprotonation of protected pyroglutamates 1(c), 1(d), and 1(e) with lithium di-isopropylamine (LDA) or lithium hexamethyldisilazide (LiHDMS) in THF, followed by reaction with electrophiles, leads to the formation of 4-substituted pyroglutamates in good yield.This approach has been used for the synthesis of the novel amino acid (4).Key Words: pyroglutamic acid; chiral amino acid synthesis
A Convenient Preparation of N-Acylpyroglutamic Acid
Imaki, Katsuhiro,Niwa, Haruki,Sakuyama, Shigeru,Okada, Takanori,Toda, Masaaki,Hayashi, Masaki
, p. 2699 - 2701 (2007/10/02)
Pyroglutamic acid reacted with acyl chloride in the presence of triethylamine in acetonitrile, yielding N-acylpyroglutamic acid without epimerization by way of mixed anhydride formation followed by intramolecular N-acylation.Keywords - angiotensin-converting enzyme; pyroglutamic acid; N-acylpyroglutamic acid; (2S)-1-pyroglutamic acid; N-acetyl-L-pyroglutamic acid
