61533-15-1Relevant academic research and scientific papers
Capto-Dative Acylenamines in the Reactions with Dialkyl Hydrogen Phosphites: One-Pot Transformation of α-Formylated Enamines to the Esters of N,N'-Disubstituted α-Aminoacids
Rulev, A. Yu.,Larina, L. I.,Voronkov, M. G.
, (2001)
α-Acylenamines with terminal double bond CH2=CH(NR2)COMe add dialkyl hydrogen phosphites to form only the Michaelis adducts. Contrary to that hydrophosphorylation of α-formylated enamines proceeds regiospecifically at C=O bond. Subsequent isomerization of
Captodative formyl enamines in a new synthesis of tertiary α-amino esters
Rulev, Alexandre Yu.,Larina, Lyudmila I.,Voronkov, Mikhail G.
, p. 892 - 899 (2001)
A strategy to create the -CH(NR2)CO- moiety from captodative formyl enamines was successfully applied to the synthesis of tertiary α-amino esters.
Synthesis, micellisation and interaction of novel quaternary ammonium compounds derived from L-Phenylalanine with 1,2-dipalmitoyl-sn-glycero- 3-phosphocholine as model membrane in relation to their antibacterial activity, and their selectivity over human red blood cells
Joondan, Nausheen,Caumul, Prakashanand,Akerman, Matthew,Jhaumeer-Laulloo, Sabina
, p. 117 - 129 (2015/02/05)
A series of quaternary ammonium compounds (QUATS) derived from L-Phenylalanine have been synthesized and their antibacterial efficiencies were determined against various strains of Gram-positive and Gram-negative bacteria. The antibacterial activity increased with increasing chain length, exhibiting a cut-off effect at C14 for Gram-positive and C12 for Gram-negative bacteria. The L-Phenylalanine QUATS displayed enhanced antibacterial properties with a higher cut-off point compared to their corresponding L-Phenylalanine ester hydrochlorides. The CMC was correlated with the MIC, inferring that micellar activity contributes to the cut-off effect in antibacterial activity. The hemolytic activities (HC50) of the QUATS against human red blood cells were also determined to illustrate the selectivity of these QUATS for bacterial over mammalian cells. In general, the MIC was lower than the HC50, and assessment of the micellar contribution to the antibacterial and hemolytic evaluation in TBS as a common medium confirmed that these QUATS can act as antibacterial, yet non-toxic molecules at their monomer concentrations. The interaction of the QUATS with the phospholipid vesicles (1,2-dipalmitoyl-sn-glycero-3-phosphocholine, DPPC) in the presence of 1-anilino-8-naphthalene sulfonate (ANS) and 1,6-diphenyl-1,3,5-hexatriene (DPH) as fluorescence probes showed that the presence of the quaternary ammonium moiety causes an increase in hydrophobic interactions, thus causing an increase in antibacterial activity.
A Straightforward Three-Component Synthesis of α-Amino Esters Containing a Phenylalanine or a Phenylglycine Scaffold
Haurena, Caroline,Le Gall, Erwan,Sengmany, Stephane,Martens, Thierry,Troupel, Michel
supporting information; experimental part, p. 2645 - 2650 (2010/07/02)
A range of α-amino esters has been synthesized in good to high yields using a straightforward three-component reaction among preformed or in situ generated aromatic or benzylic organozinc reagents, primary or secondary amines, and ethyl glyoxylate. The procedure, which is characterized by its simplicity, allows the concise synthesis of esters bearing a phenylglycine or a phenylalanine scaffold.
A concise three-component synthesis of α-amino esters derived from phenylglycine and phenylalanine
Haurena, Caroline,Sengmany, Stéphane,Huguen, Paul,Gall, Erwan Le,Martens, Thierry,Troupel, Michel
body text, p. 7121 - 7123 (2009/04/10)
α-Amino esters have been synthesized using a straightforward three-component reaction among preformed or in situ-generated aromatic or benzylic organozinc reagents, primary or secondary amines and ethyl glyoxylate. The procedure, which is characterized by its simplicity, allows the concise synthesis of phenylglycine and phenylalanine derivatives.
Transformations des enamines α-formylees: Synthese d'α-amino esters N,N-disubstitues
Rulev, Alexander Yu.,Larina, Lyudmila I.,Voronkov, Mikhail G.
, p. 10211 - 10214 (2007/10/03)
2-Dialkylaminoalkanoic esters are prepared in moderate yield by the reaction of N,N-disubstituted 2-amino-2-alkenals with dialkyl phosphonates in the presence of sodium alkoxide. A mechanism involving an α-keto-β-aminophosphonate as an intermediate is proposed. (C) 2000 Elsevier Science Ltd.
