Aminobenzylation d'aldéhydes phosphoniques: préparation d'acides aminoalkylphosphoniques

1981 ◽  
Vol 59 (19) ◽  
pp. 2864-2869 ◽  
Author(s):  
Geneviève Fabre ◽  
Noël Collignon ◽  
Philippe Savignac
Keyword(s):  
Amino Acids ◽  
Catalytic Hydrogenation ◽  
Reductive Amination ◽  
Reducing Agent ◽  
Amino Esters ◽  
Hydrolysis Of

The reaction of phosphonic aldehydes with benzylamine in presence of NaBH3CN yields benzylaminoalkylphosphonates which, submitted to catalytic hydrogenation, lead to phosphonic amino esters. When reductive amination is carried out with H2/Pd reduction and debenzylation are observed simultaneously. In the absence of reducing agent the enaminobenzylphosphonate can be isolated and N-alkylated. Hydrolysis of phosphonic amino-esters with dilute HCl gives phosphonic amino acids. The order of occurrence of each operation, as well as the choice of the catalyst is discussed.

Synthèse et amination réductrice de phosphonopyruvates: préparation d'acides amino-2 carboxy-2 alkylphosphoniques (β-phosphonoalanine)

1979 ◽  
Vol 57 (24) ◽  
pp. 3216-3220 ◽  
Author(s):  
Jean-Marie Varlet ◽  
Noël Collignon ◽  
Philippe Savignac
Keyword(s):  
Amino Acids ◽  
Reductive Amination ◽  
Primary Amines ◽  
Amino Esters

The reaction of α-copper(I)alkanephosphonates with methyl and ethyl oxalyl chlorides gives methyl or ethyl dialkylphosphonopyruvates which, submitted to reductive amination in ethanol at pH 6–7 with sodium cyanohydridoborate (NaBH3CN) and ammonia, or primary amines, lead to phosphonic amino esters; hydrolysis with diluted HCl gives phosphonic amino acids. These three reactions constitute a general way to β-phosphonoalanine and β-alkyl β-phosphonoalanine.

scholarly journals Efficient Synthesis of New Fluorinated β-Amino Acid Enantiomers through Lipase-Catalyzed Hydrolysis

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 5990
Author(s):  
Sayeh Shahmohammadi ◽  
Ferenc Fülöp ◽  
Enikő Forró
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Ester Hydrochloride ◽  
Enzymatic Method ◽  
Efficient Synthesis ◽  
Preparative Scale ◽  
Carboxylic Ester ◽  
Amino Acid Enantiomers ◽  
Amino Esters ◽  
Hydrolysis Of

An efficient and novel enzymatic method has been developed for the synthesis of β-fluorophenyl-substituted β-amino acid enantiomers through lipase PSIM (Burkholderia cepasia) catalyzed hydrolysis of racemic β-amino carboxylic ester hydrochloride salts 3a–e in iPr2O at 45 °C in the presence of Et3N and H2O. Adequate analytical methods were developed for the enantio-separation of racemic β-amino carboxylic ester hydrochlorides 3a–e and β-amino acids 2a–e. Preparative-scale resolutions furnished unreacted amino esters (R)-4a–e and product amino acids (S)-5a–e with excellent ee values (≥99%) and good chemical yields (>48%).

Deinking of recycled paper by coupling of the enzyme endo-β-1,4-D-glucanasa and the cellulose, and by using a laboratory flotation column

MRS Advances ◽  
2020 ◽  
Vol 5 (52-53) ◽  
pp. 2669-2678
Author(s):  
Jeovani González P. ◽  
Ramiro Escudero G
Keyword(s):  
Amino Acids ◽  
Sodium Hydroxide ◽  
Paper Industry ◽  
Computational Simulation ◽  
Cellulose Fibers ◽  
Residual Water ◽  
Chemical Reagent ◽  
Recycled Paper ◽  
Flotation Column ◽  
Hydrolysis Of

AbstractDeinking of recycled office (MOW) paper was carried out by using a flotation column and adding separately sodium hydroxide, and the enzyme Cellulase Thricodema Sp., as defibrillators.The de-inked cellulose fibers were characterized according to the standards of the paper industry, to compare the efficiency of the deinking of each chemical reagent used to hydrolyze the fibers and defibrillate them.The computational simulation of the molecular coupling between the enzyme and cellulose was performed, to establish the enzyme-cellulose molecular complex and then to identify the principal amino-acids of endo-β-1,4-D-glucanase in this molecular link, which are responsible for the hydrolysis of the cellulose.Experimental results show the feasibility to replace sodium hydroxide with the enzyme Cellulase Thricodema Sp., by obtaining deinked cellulose with similar optical and physical properties.The use of the enzyme instead of sodium hydroxide avoids the contamination of the residual water; in addition to that, the column is operated more easily, taking into consideration that the pH of the system goes from alkaline to neutral.

Exogenous Directing Group Free, Ligand-Enabled gamma-C(sp3)–H Arylation of Free Primary Aliphatic Amines and α-Amino Esters

2019 ◽  
Author(s):  
Yongzheng Ding ◽  
Shuai Fan ◽  
Xiaoxi Chen ◽  
yuzhen gao ◽  
Gang Li
Keyword(s):  
Amino Acids ◽  
Large Scale ◽  
Free Ligand ◽  
Aliphatic Amines ◽  
Rapid Synthesis ◽  
Amino Esters ◽  
Directing Group ◽  
Large Scale Synthesis ◽  
Primary Aliphatic Amines

A Pdᴵᴵ-catalyzed, ligand-enabled gamma-C(sp3)–H arylation of free primary aliphatic amines and amino esters without using an exogenous directing group is reported. This reaction is compatible with unhindered free aliphatic amines, and it is also be applicable to the rapid synthesis of biologically and synthetically valuable unnatural α-amino acids. Large scale synthesis is also feasible using this method.<br>

Studies on Chromatographic Fractioning by Cations Exchangers of a Bovine Hemoglobin Hydrolysate

2018 ◽  
Vol 69 (10) ◽  
pp. 2794-2798
Author(s):  
Alina Diana Panainte ◽  
Ionela Daniela Morariu ◽  
Nela Bibire ◽  
Madalina Vieriu ◽  
Gladiola Tantaru ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Amino Acids ◽  
Retention Time ◽  
Chromatographic Separation ◽  
Bovine Hemoglobin ◽  
Reverse Phase ◽  
Hplc System ◽  
Fast Flow ◽  
Hydrolysis Of ◽  
Phase Column

A peptidic hydrolysate has been obtained through hydrolysis of bovine hemoglobin using pepsin. The fractioning of the hydrolysate was performed on a column packed with CM-Sepharose Fast Flow. The hydrolysate and each fraction was filtered and then injected into a HPLC system equipped with a Vydak C4 reverse phase column (0.46 x 25 cm), suitable for the chromatographic separation of large peptides with 20 to 30 amino acids. The detection was done using mass spectrometry, and the retention time, size and distribution of the peptides were determined.

scholarly journals C-N Bond Formation by Consecutive Continuous-Flow Reductions towards A Medicinally Relevant Piperazine Derivative

Molecules ◽  
2021 ◽  
Vol 26 (7) ◽  
pp. 2040
Author(s):  
Zsolt Fülöp ◽  
Péter Bana ◽  
István Greiner ◽  
János Éles
Keyword(s):  
Antipsychotic Drug ◽  
Catalytic Hydrogenation ◽  
Continuous Flow ◽  
Reductive Amination ◽  
Reduction Method ◽  
Bond Formation ◽  
Aluminum Salt ◽  
Line Extraction ◽  
Piperazine Derivative ◽  
Step Procedure

A new, continuous-flow consecutive reduction method was developed for the C-N bond formation in the synthesis of the key intermediate of the antipsychotic drug cariprazine. The two-step procedure consists of a DIBAL-H mediated selective ester reduction conducted in a novel, miniature alternating diameter reactor, followed by reductive amination using catalytic hydrogenation on 5% Pt/C. The connection of the optimized modules was accomplished using an at-line extraction to prevent precipitation of the aluminum salt byproducts.

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