15911-73-6Relevant academic research and scientific papers
Asymmetric Synthesis of α-Amino Acids by Organocatalytic Biomimetic Transamination
Kang, Qi-Kai,Selvakumar, Sermadurai,Maruoka, Keiji
supporting information, p. 2294 - 2297 (2019/04/10)
A biomimetic enantioselective transamination of α-keto ester derivatives can be realized under mild conditions by using chiral quaternary ammonium arenecarboxylates in the absence of base additives. The corresponding α-amino acids can be used as versatile intermediates for further synthetic transformations that furnish chiral pyrrolidine and octahydroindolizine derivatives.
A practical aryl unit for azlactone dynamic kinetic resolution: Orthogonally protected products and a ligation-inspired coupling process
Tallon, Sean,Manoni, Francesco,Connon, Stephen J.
supporting information, p. 813 - 817 (2015/02/19)
The first strategy for bringing about enantioselective azlactone dynamic kinetic resolution to generate orthogonally protected amino acids has been developed. In the presence of a C2-symmetric squaramide-based catalyst, benzyl alcohol reacts with novel yet readily prepared tetrachloroisopropoxycarbonyl-substituted azlactones to generate trapped phthalimide products of significant synthetic interest with excellent enantiocontrol. These materials are masked amino acids which are demonstrably orthogonally protected: cleavage of the phthalimide can be achieved in the presence of the ester and vice versa. This process could be utilized to bring about a highly stereoselective ligation-type coupling of protected serines (at stoichiometric loadings) with racemic azlactones derived from both natural and abiotic amino acids. After deprotection, a subsequent base-mediated Oa??N acyl transfer occurs to form a dipeptide.
Novel Analogs of Camptothecin
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, (2014/05/20)
The present invention provides novel conjugates of camptothecin and camptothecin analogs with a linker and an HSA-binding moiety. The novel conjugates are prodrug forms of the camptothecin or camptothecin analogs and can be used to treat mammalian cell pr
SOLUBLE COMPLEXES OF DRUG ANALOGS AND ALBUMIN
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Page/Page column 38-39, (2014/08/19)
The present invention provides novel, non-covalently bound complexes of serum albumin and analogs of poorly soluble drugs, such as camptothecin. The novel complexes are significantly more water-soluble than the camptothecin analogs and are useful as prodr
The effect of benzyl amine on the efficiency of the base-catalyzed transamination of α-keto esters
Xue, Fazhen,Xiao, Xiao,Wang, Haining,Shi, Yian
experimental part, p. 6862 - 6867 (2012/08/28)
This paper describes the effect of benzyl amine on the base-catalyzed transamination of α-keto esters. Among various benzyl amines examined, o-HOC6H4CH2NH2 was found to be highly effective for the reaction, affording a wide variety of α-amino esters in good yields. The o-OH group of the benzyl amine facilitates the transamination process likely via H-bond. Moderate enantiomeric excess was obtained for α-amino ester when a quinine derived catalyst was used.
Studies on the enantioselective synthesis of α-amino acids via asymmetric phase-transfer catalysis
Lygo,Crosby,Lowdon,Peterson,Wainwright
, p. 2403 - 2409 (2007/10/03)
In this paper, we describe investigations into the use of cinchona alkaloid-derived quaternary ammonium phase-transfer catalysts for the asymmetric alkylation of a benzophenone-derived glycine-imine. Utility of this process is demonstrated by the enantioselective synthesis of a range of α-amino acid esters.
A new class of asymmetric phase-transfer catalysts derived from Cinchona alkaloids - Application in the enantioselective synthesis of α-amino acids
Lygo, Barry,Wainwright, Philip G.
, p. 8595 - 8598 (2007/10/03)
A new class of Cinchona alkaloid-derived quaternary ammonium phase-transfer catalysts bearing a N-anthracenylmethyl function are presented. These catalysts show high stereocontrol in the asymmetric alkylation of a benzophenone-derived glycine-imine, and application of this process to the enantioselective synthesis of a range of α-amino acid esters (e.e. 67-94%) is investigated.
Chemoselective N-deprotection of tert-butyl 2-(trifluoroacetylamino) esters under PTC conditions: Synthesis of tert-butyl 2-aminocarboxylates
Albanese, Domenico,Corcella, Francesco,Landini, Dario,Maia, Angelamaria,Penso, Michele
, p. 247 - 249 (2007/10/03)
Trifluoroacetamide 1 is alkylated in good yields (77-83%) by tert-butyl 2-bromocarboxylates 3 under solid-liquid phase transfer catalysis (PTC) conditions [anhydrous K2CO3, triethyl(benzyl)ammonium chloride (TEBA; 10%), MeCN, 80°C]. The resulting tert-butyl 2-(trifluoroacetylamino) carboxylates 5 are chemoselectively hydrolysed in 75-95% yields to the corresponding tert-butyl 2-amino carboxylates, isolated as hydrochlorides 8, under liquid-liquid PTC conditions [CH2Cl2 or Et2O, aqueous 20% KOH, TEBA (10%), 25-40°C].
N-ACYLAMINO ACID DERIVATIVES AND THEIR PHARMACEUTICAL COMPOSITIONS
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, (2008/06/13)
An N-acylamino acid derivative of the formula: STR1 wherein the substituents are herein defined or a salt thereof, which is useful as hypotensive drugs.
NEW SYNTHESIS OF DL-α-AMINOACIDS FROM t-BUTYL N(DIPHENYLMETHYLENE) OXAMATE
Bazureau, J.P.,Person, D.,Corre, M. Le
, p. 3065 - 3068 (2007/10/02)
The condensation of phosphorus ylids with t-butyl N(diphenylmethylene) oxamate gives 2-aza 1,3-dienes ; subsequent reduction with sodium cyanoborohydride provides protected α-aminoacids.
