- COMPOSES CETONIQUES SUPPORTES CATALYSEURS D'HYDRATATION DES α-AMINONITRILES
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The preparation of hydrophilic crosslinked polymers which are carrying carbonyl groups of the 4-piperidone type is described.These compounds catalyse the hydration of α-aminonitriles to α-aminoamides.The main parameters involved in the catalytic activity are studied.
- Sola, R.,Brugidou, J.,Taillades, J.,Commeyras, A.,Previero, A.
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- Method for catalytically synthesizing acrylamide compound by MOFs-derived zirconium-based ternary oxide solid acid
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The invention provides a catalytic synthesis of acrylamide compounds with zirconium-based ternary oxide solid acid as a catalyst, and the low-temperature activity is good. In the synthesis process, the acid is small, the reaction conditions are mild and controllable, the byproducts are few, the reaction yield is effectively improved, the purity is high, the quality is good, and the method is suitable for large-scale production.
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Paragraph 0069-0072
(2021/11/14)
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- Preparation method of acrylamide-based compounds
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The present invention relates to the field of fine chemical materials, particularly to a new mild, efficient and economical preparation process technology of a class of acrylamide-type compounds, wherein a beta-amine substituted propionamide precursor is subjected to an in-situ amine elimination reaction under the action of a suitable electrophilic reagent so as to prepare the target product.
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Paragraph 0017
(2018/01/11)
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- A divergent synthesis of new aliphatic poly(ester-amine) dendrimers bearing peripheral hydroxyl or acrylate groups
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A novel class of aliphatic poly(ester-amine) dendrimers, bearing hydroxyl or acrylate peripheral groups, was designed and synthesized via a divergent strategy using readily available piperazine, diethanolamine and acryloyl chloride as the monomeric building blocks.
- Sha, Yaowu,Shen, Liang,Hong, Xiaoyin
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p. 9417 - 9419
(2007/10/03)
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- Total synthesis of amiclenomycin, an inhibitor of biotin biosynthesis.
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We describe the first synthesis of amiclenomycin, a natural product that has been found to inhibit biotin biosynthesis and, as a consequence, to exhibit antibiotic properties. Structure 1, with a trans relationship between the ring substituents. had previously been proposed for amiclenomycin on the basis of its 1H NMR spectrum. We have prepared the trans and cis isomers 1 and 2 by unequivocal routes and we conclude that the natural product is in fact the cis isomer 2. The properly substituted cyclohexadienyl rings were constructed first. A cycloaddition reaction between 1,2-di(phenylsulfonyl)ethylene and the N-allyloxycarbonyl diene 13, followed by reductive elimination of the phenylsulfinyl groups, gave the cis isomer 15. To obtain the trans isomer, the O-trimethylsilyl diene was used to give the cis hydroxylated Diels-Alder adduct 33, which was transformed into the corresponding trans amino derivative by means of a Mitsunobu reaction. The L-alpha-amino acid functionality was introduced by means of a Strecker reaction on the aldehydes 16 and 42, followed by enzymatic hydrolysis with immobilised pronase.
- Mann, Stephane,Carillon, Sophie,Breyne, Olivier,Marquet, Andree
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p. 439 - 450
(2007/10/03)
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- Deracemization process of α-aminoesters via pyridoxal. II.- Study of copolymerization of polymerizable forms of pyridoxal. Reactivity of corresponding polymers
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We studied the copolymerization of pyridoxal (PL) polymerizable forms, in the presence of two different comonomers (a diluting and crosslinking agent) and the catalytic activity of the corresponding polymers on the α-aminoester racemization.We discuss the choice of these comonomers in the polymerization and also their concentration.Thus, using 4-acryloylmorpholine as a diluting agent, we obtained a sufficiently hydrophilic polymer in an aqueous medium, and the partion coefficient of the substrate was more favorable.In addition, polymer IV, in which the arm allowing immobilization of PL is most distant from the catalytic site, had the highest activity.Keywords: racemization / α-aminoester / pyridoxal analogues / covalent immobilization / polyacrylamide support / radical polymerization
- Honnoraty, Anne-Marie,Mion, Louis,Rousset, Alain,Taillades, Jacques,Commeyras, Auguste
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p. 721 - 728
(2007/10/02)
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- La pronase immobilisee sur poly(N-acryloylpiperidin-4-one): un catalyseur d'hydrolyse L-enantiospecifique des α-aminonitriles
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Pronase immobilized on poly(N-acryloylpiperidin-4-one) : a L-enantiospecific hydrolysis of α-aminonitriles with immobilized amidase. α-Aminonitriles are not substrates for pronase (an amidase) in the homogeneous phase but become substrates for pronase when it is immobilized on polymer matrix with ketonic sites (piperidin-4-one).In this paper we show that under low basic aqueous conditions (pH 10-11), the hydration of α-aminonitriles can be efficiently catalyzed by poly(N-acryloylpiperidin-4-one) crosslinked with 1,4-bis acryloylpiperazine (A(80:20)) in the presence of phosphate or borate buffers.These conditions comply with the hydrolysis of α-aminoamides by pronase immobilized on poly(N-acryloylpiperidin-4-one)crosslinked with 1,4-bis(acryloyl)piperazine (A(80:20/p).Thus, in a buffered borate solution at pH 10.5, α(DL)-aminonitrile is enantiospecifically hydrolyzed into α(D)-aminoamide and α(L)-amino acid. Key words: α-aminonitriles / α amino acids / L-enantiospecific hydrolysis / polymer-supported catalysis / nitrilasic activity
- Taillades, Jacques,Garrel, Laurence,Guillen, Franck,Collet, Helene,Commeyras, Auguste
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p. 119 - 127
(2007/10/02)
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- Enzymatic hydrolysis of DL-phenylalaninamide with pronase immobilized on ketonic polymer.
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In the transformation of an aldehyde into an α-aminoacid (Strecker's reaction or related), we try to enantioselectively hydrolyse the α-aminonitrile intermediate using a catalyst obtained by the immobilization of pronase on chemically reactive polymer presenting piperidone groups.This catalyst should be able to simultaneously hydrate the α-aminonitrile and to enantioselectively hydrolyse the α-aminoamide obtained. First of all, we define the essential parameters of this reaction (pH, substrat concentration, catalyst mass) by a kinetic study.These parameters determine the activity of immobilized pronase in the enantioselective hydrolysis of DL-phenylalaninamide. immobilized enzyme / α-aminoamide / enantioselective hydrolysis / ketonic polymer
- Taillades, J.,Boussac, P.,Collet, H.,Brugidou, J.,Commeyras, A.
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p. 423 - 429
(2007/10/02)
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- One step process for preparing cross-linked poly-β-alanine microspheres from acrylamide and a copolymerisable polyfunctional compound
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A one-step process for preparing cross-linked poly-β-alanine as microspheres having narrow size distribution comprises polymerizing acrylamide with a polyfunctional compound copolymerizable with acrylamide (with the polyfunctional compound also acting as the cross-linking agent) in an organic solvent or a mixtured such solvents in the presence of an ionic polymerization initiator and a suspension agent. The resulting microspheres may be impregnated with a pharmaceutically or cosmetically active substance.
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