113400-36-5Relevant articles and documents
A concise asymmetric route to the bridged bicyclic tropane alkaloid ferruginine using enyne ring-closing metathesis
Aggarwal, Varinder K.,Astle, Christopher J.,Rogers-Evans, Mark
, p. 1469 - 1471 (2004)
Enyne metathesis has been used to prepare bridged azabicycles and applied in a short asymmetric synthesis of the tropane ferruginine. A Grubbs first generation catalyst proved to be superior to the second generation catalyst in the enyne metathesis reaction.
Synthesis of benzyl (6S)-1,3-dichloro-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrazine-6- carboxylic ester, a new conformationally constrained peptidomimetic derivative
Gloanec, Philippe,Hervé, Yolande,Brémand, Nathalie,Lecouvé, Jean-Pierre,Bréard, Fabienne,De Nanteuil, Guillaume
, p. 3499 - 3501 (2002)
We describe the synthesis of benzyl (6S)-1,3-dichloro-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrazine-6- carboxylic ester, a new conformationally constrained peptidomimetic derivative. This compound is prepared in seven steps from (S)-pyroglutamic acid as starting material.
Enantiopure 5-CF3-Proline: Synthesis, Incorporation in Peptides, and Tuning of the Peptide Bond Geometry
Sanchez, Clément A.,Gadais, Charlène,Chaume, Grégory,Girard, Sylvaine,Chelain, Evelyne,Brigaud, Thierry
, p. 382 - 387 (2021/01/13)
The straightforward synthesis of enantiopure 5-(R)-and 5-(S)-trifluoromethylproline is reported. The key steps are a Ruppert-Prakash reagent addition on l-pyroglutamic esters followed by an elimination reaction and a selective reduction. The solution-phase and solid-phase incorporation of this unprotected enantiopure fluorinated amino acid in a short peptide chain was demonstrated. Compared to proline, the CF3 group provides a decrease of the trans to cis amide bond isomerization energy and an increase of the cis conformer population.
Synthesis of the Siderophore Coelichelin and Its Utility as a Probe in the Study of Bacterial Metal Sensing and Response
Williams, Jade C.,Sheldon, Jessica R.,Imlay, Hunter D.,Dutter, Brendan F.,Draelos, Matthew M.,Skaar, Eric P.,Sulikowski, Gary A.
, p. 679 - 682 (2019/02/07)
A convergent total synthesis of the siderophore coelichelin is described. The synthetic route also provided access to acetyl coelichelin and other congeners of the parent siderophore. The synthetic products were evaluated for their ability to bind ferric iron and promote growth of a siderophore-deficient strain of the Gram-negative bacterium Pseudomonas aeruginosa under iron restriction conditions. The results of these studies indicate coelichelin and several derivatives serve as ferric iron delivery vehicles for P. aeruginosa.
A high-quality N - tert-butoxycarbonyl - L - pyroglutamic acid benzyl ester industrial production method
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Paragraph 0022; 0025-0027; 0030-0032; 0035-0037; 0040-0041, (2019/05/16)
The invention relates to a bio-chemical technology field, in particular to a high-quality N - tert-butoxycarbonyl - L - pyroglutamic acid benzyl ester industrial production method, the raw material capture and L - pyroglutamic acid in the presence of a catalyst, with the chlorinated animal pen or bromination animal pen reaction to obtain the intermediate L - pyroglutamic acid benzyl ester; intermediate L - pyroglutamic acid benzyl ester organic phase under the catalyst condition, with the Boc anhydride reaction, to obtain the target crude N - tert-butoxycarbonyl - L - pyroglutamic acid benzyl ester; crude N - tert-butoxycarbonyl - L - pyroglutamic acid benzyl ester, in mixed crystals in the recrystallization solvent, for obtaining high-purity N - tert-butoxycarbonyl - L - pyroglutamic acid benzyl ester. Compared with the prior process, the present invention provides N - tert butoxycarbonyl - L - pyroglutamic acid benzyl ester industrial production method has the advantages of: can be efficient, stable production of the high-quality powder N - tert butoxycarbonyl - L - pyroglutamic acid benzyl ester, the purity is greater than 99.5%, a single impurities less than 0.1%.
Green preparation method of N-substituted-L-pyroglutamate
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Paragraph 0055; 0056; 0058; 0059; 0066; 0067, (2018/03/28)
The invention provides a green preparation method of N-substituted-L-pyroglutamate. The method comprises the steps as follows: L-glutamic acid diester hydrochloride (III) is prepared from L-glutamic acid (II) as a starting material in the presence of an acidic reagent by an esterification reaction; then, L-glutamic acid diester hydrochloride (III) is subjected to N-substituted protective reactionwith an N-substituent protective reagent with a one-pot method in the presence of a base and a solvent, an N-substituted protective group is introduced, heating is performed for dealcoholization cyclization in molecules, and N-substituted-L-pyroglutamate as shown in the formula (I) is obtained. The method has the advantages of cheap and easily available raw materials, classic reaction types, shortprocess route, simple and convenient operation, small waste water amount, green and environment-friendly production process, high reaction yield and low product cost. 5R-benzyloxyaminopiperidine-2S-carboxylate, 5R-benzyloxyaminopiperidine-2S-formate ethanedioate and avibactam can be prepared from N-substituted-L-pyroglutamate as shown in the formula (I).
A new class of non-C2-symmetric ligands for oxidative and redox-neutral palladium-catalyzed asymmetric allylic alkylations of 1,3-diketones
Trost, Barry M.,Donckele, Etienne J.,Thaisrivongs, David A.,Osipov, Maksim,Masters, James T.
, p. 2776 - 2784 (2015/03/04)
We report the discovery, synthesis, and application of a new class of non-C2-symmetric phosphoramidite ligands derived from pyroglutamic acid for use in both oxidative and redox-neutral palladium-catalyzed asymmetric allylic alkylations of 1,3-diketones. The resulting chiral products are typically obtained in high yield with good to excellent levels of enantioselectivity.
THIOPHOSPHATE NUCLEOSIDES FOR THE TREATMENT OF HCV
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, (2014/09/16)
Provided herein are compounds, compositions and methods for the treatment of Flaviviridae infections, including HCV infections. In certain embodiments, the compounds are according to Formula 2001: where PD, Base, RA and RB are as provided herein. In certain embodiments, compounds and compositions of nucleoside derivatives are disclosed, which can be administered either alone or in combination with other anti-viral agents.
Synthesis and evaluation of novel orally active p53-MDM2 interaction inhibitors
Miyazaki, Masaki,Naito, Hiroyuki,Sugimoto, Yuuichi,Yoshida, Keisuke,Kawato, Haruko,Okayama, Tooru,Shimizu, Hironari,Miyazaki, Masaya,Kitagawa, Mayumi,Seki, Takahiko,Fukutake, Setsuko,Shiose, Yoshinobu,Aonuma, Masashi,Soga, Tsunehiko
, p. 4319 - 4331 (2013/07/27)
We have discovered and reported potent p53-MDM2 interaction inhibitors possessing dihydroimidazothiazole scaffold. Our lead showed strong activity in vitro, but did not exhibit antitumor efficacy in vivo for the low metabolic stability. In order to obtain orally active compounds, we executed further optimization of our lead by the improvement of physicochemical properties. Thus we furnished optimal compounds by introducing an alkyl group onto the pyrrolidine at the C-2 substituent to prevent the metabolism; and modifying the terminal substituent of the proline motif improved solubility. These optimal compounds exhibited good PK profiles and significant antitumor efficacy with oral administration on a xenograft model using MV4-11 cells having wild type p53.
LIGAND-DIRECTED COVALENT MODIFICATION OF PROTEIN
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Page/Page column, (2013/03/26)
The present invention relates to enzyme inhibitors. More specifically, the present invention relates to ligand-directed covalent modification of proteins; method of designing same; pharmaceutical formulation of same; and method of use.
