- Method for synthesizing acrylamide derivative
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The invention relates to a method for synthesizing an acrylamide derivative from alkyl primary amine and acrylamide as raw materials and belongs to the field of chemical product synthesis methods. Themethod for synthesizing the acrylamide derivative comprises the following steps: 1) under conditions of 150-160 DEG C and 0.6-1MPa, conducting a Diels-Alder reaction on acrylamide and anthracene so as to obtain an acrylamide addition intermediate of 1:1; 2) conducting backflowing on the addition intermediate, alkyl primary amine and a catalyst for 6-20 hours at 50-180 DEG C, and conducting an amino exchange reaction so as to obtain an acrylamide derivative addition intermediate; and 3) carrying out thermal cracking on the acrylamide derivative addition intermediate at 150-180 DEG C and 1-3kPa, conducting rectification so as to obtain an acrylamide derivative, conducting sublimation recycling on anthracene, and repeating the process. The method for synthesizing the acrylamide derivative, which is provided by the invention, is free of liquid solvent, is capable of effectively reducing the content of VOCs (volatile organic compounds) in the generation process, and is simple in reaction process, easy in product and recycling raw material separation, easy in reaction condition control, high in security, high in reaction yield, small in byproduct amount, simple in aftertreatment, high in product purity and easy in industrial production.
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Paragraph 0029; 0047; 0051
(2019/10/01)
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- Transiently Thermoresponsive Acetal Polymers for Safe and Effective Administration of Amphotericin B as a Vaccine Adjuvant
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The quest for new potent and safe adjuvants with which to skew and boost the immune response of vaccines against intracellular pathogens and cancer has led to the discovery of a series of small molecules that can activate Toll-like receptors (TLRs). Whereas many small molecule TLR agonists cope with a problematic safety profile, amphotericin B (AmpB), a Food and Drug Administration approved antifungal drug, has recently been discovered to possess TLR-triggering activity. However, its poor aqueous solubility and cytotoxicity at elevated concentrations currently hampers its development as a vaccine adjuvant. We present a new class of transiently thermoresponsive polymers that, in their native state, have a phase-transition temperature below room temperature but gradually transform into fully soluble polymers through acetal hydrolysis at endosomal pH values. RAFT polymerization afforded well-defined block copolymers that self-assemble into micellar nanoparticles and efficiently encapsulate AmpB. Importantly, nanoencapsulation strongly reduced the cytotoxic effect of AmpB but maintained its TLR-triggering capacity. Studies in mice showed that AmpB-loaded nanoparticles can adjuvant an RSV vaccine candidate with almost equal potency as a highly immunogenic oil-in-water benchmark adjuvant.
- Van Herck, Simon,Van Hoecke, Lien,Louage, Benoit,Lybaert, Lien,De Coen, Ruben,Kasmi, Sabah,Esser-Kahn, Aaron P.,David, Sunil A.,Nuhn, Lutz,Schepens, Bert,Saelens, Xavier,De Geest, Bruno G.
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p. 748 - 760
(2017/12/18)
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- MANUFACTURING METHOD OF β-SUBSTITUTED PROPIONIC ACID AMIDE AND N-SUBSTITUTED (METH)ACRYLAMIDE
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PROBLEM TO BE SOLVED: To provide a method for industrially manufacturing β-alkoxy propionic acid amide, β-amino propionic acid amide and N-substituted (meth)acryl amide using (meth)acrylic acid ester as starting material at high yield and high purity. SOLUTION: There is provided a method for obtaining N-substituted (meth)acryl amide represented by target compound formula (7) by conducting an amidation reaction with amine using β-substituted propionic acid ester represented by the formula (1) of a product of a Michael addition reaction of (meth)acrylic acid ester and alcohol or amine in presence of a metal complex as a catalyst to obtain β-substituted propionic acid amide represented by the formula (3) and conducting a thermal decomposition reaction of β-substituted propionic acid amide in presence of the metal complex as the catalyst to eliminate alcohol or amine. A-CH2-C(R1)H-C(=O)-OR2 (1), A-CH2-C(R1)H-C(=O)-N(R3)R4 (3), CH2=C(R1)-C(=O)-N(R3)R4 (7) SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0055; 0057; 0060; 0064
(2018/07/03)
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- Hydrophobic Nanoparticles Reduce the β-Sheet Content of SEVI Amyloid Fibrils and Inhibit SEVI-Enhanced HIV Infectivity
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Semen-derived enhancer of virus infection (SEVI) fibrils are naturally abundant amyloid aggregates found in semen that facilitate viral attachment and internalization of human immunodeficiency virus (HIV) in cells, thereby increasing the probability of infection. Mature SEVI fibrils are composed of aggregated peptides exhibiting high β-sheet secondary structural characteristics. Herein, we show that polymers containing hydrophobic side chains can interact with SEVI and reduce its β-sheet content by ~45% compared with the β-sheet content of SEVI in the presence of polymers with hydrophilic side chains, as estimated by polarization modulation-infrared reflectance absorption spectroscopy measurements. A nanoparticle (NP) formulation of this hydrophobic polymer reduced SEVI-mediated HIV infection in TMZ-bl cells by 60% compared with the control treatment. Although these NPs lacked specific amyloid-targeting groups, thus requiring high concentrations to observe biological activity, the use of hydrophobic interactions to alter the secondary structure of amyloids represents a useful approach to neutralizing the SEVI function. These results could, therefore, have general implications in the design of novel materials that can modify the activity of amyloids associated with a variety of other neurological and systemic diseases.
- Sheik, Daniel A.,Chamberlain, Jeffrey M.,Brooks, Lauren,Clark, Melissa,Kim, Young Hun,Leriche, Geoffray,Kubiak, Clifford P.,Dewhurst, Stephen,Yang, Jerry
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p. 2596 - 2602
(2017/03/20)
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- Method for preparing N-hydroxyethyl acrylamide
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The invention discloses a method for preparing N-hydroxyethyl acrylamide. Acrylic anhydride and amino-ethanol perform reaction mildly at low temperature. Acrylic acid serving as a byproduct and a product are separated in distillation mode. The N-hydroxyethyl acrylamide obtained by the method has high purity and high yield, and the production process is simple and easily available.
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Paragraph 0017; 0018; 0019; 0020; 0021; 0022
(2017/10/28)
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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 0021
(2018/01/11)
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- METHOD FOR PRODUCING 2-HYDROXYALKYL (METH) ACRYLAMIDE
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PROBLEM TO BE SOLVED: To provide a method for producing N-(2-hydroxyalkyl)(meth) acrylamide. SOLUTION: The reaction of a ketimine compound or an aldimine compound of 2-aminoalkyl (meth) acrylate with water makes it possible to produce N-(2-hydroxyalkyl)(meth) acrylamide with high yields. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0039
(2017/06/02)
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- METHOD FOR PRODUCING N-SUBSTITUTED (METH)ACRYLAMIDE
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PROBLEM TO BE SOLVED: To provide an industrial method for efficiently producing a high-purity N-substituted (meth)acrylamide in a short time even under mild reaction conditions, which uses (meth)acrylic acid as a starting material and generates only water as a byproduct. SOLUTION: There is provided a method for producing an N-substituted (meth)acrylamide to obtain an objective compound, N-substituted (meth)acrylamide by the step of: reacting a (meth)acrylic and an amine compound to synthesize an aminopropionic acid derivative; then adding an inorganic material composed mainly of silica as a catalyst and performing amidation with the same amine compound to obtain an aminopropionic acid derivative; and subsequently eliminating an amine by the thermal decomposition reaction. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0053; 0056; 0057
(2018/11/22)
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- (Meth) acrylamide N-substituted (by machine translation)
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PROBLEM TO BE SOLVED: a (meth) acrylic acid and a starting material, high yield, high-purity (meth) and N-substituted carboxylic acid amide derivative norbonene alkylacrylamide industrial production method. SOLUTION: and (meth) acrylic acid aminopentadienoic cyclometallized Diels-Alder reaction product of, norbonene carboxylic acid derivative, and silica as a main catalyst in the presence of an inorganic material, and amide-amine compound, norbonene carboxylic acid amide derivative. Furthermore, the vapor phase of the norbonene vinylcarboxamide deriv. aminopentadienoic cyclometallized by thermal decomposition reaction by desorbing, (meth) acrylamide purpose compd. N-substituted. Selected drawing: no (by machine translation)
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Paragraph 0054; 0055; 0056; 0057
(2018/12/12)
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- METHOD FOR PRODUCING N-SUBSTITUTED (METH)ACRYLAMIDE
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PROBLEM TO BE SOLVED: To provide an industrial method for producing a high-purity alkoxy propionic acid amide derivative and N-substituted (meth)acrylamide in a high yield, which uses a (meth)acrylic acid as a starting material. SOLUTION: There is provided a method for producing an objective compound, N-substituted (meth)acrylamide by the step of: amidating an alkoxy propionic acid derivative, which is synthesized from a (meth)acrylic acid and alcohol and represented by the formula [1], with an amine compound; R3-NH-R4(R3 and R4 each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms or may form a saturated 5- to 7-membered ring with a nitrogen atom supporting them) in the presence of an inorganic material composed mainly of silica as a catalyst to obtain an alkoxy propionic acid amide derivative; and eliminating alcohol by the liquid phase thermal decomposition reaction of the alkoxy propionic acid amide derivative. (R1 represents H or a methyl group; and R2 represents a linear or branched alkyl group having 1 to 6 carbon atoms or an alkenyl group.) COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0057; 0060
(2017/01/05)
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- (Meth) acrylamide hydroxyakyl production (by machine translation)
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PROBLEM TO BE SOLVED: To provide a method of manufacturing hydroxyalkyl (meth) acrylamide which uses dibutyl amine as a double bond protecting reagent, and thereby can stably carry out thermal decomposition of an amide adduct without an acid catalyst. SOLUTION: In the method, methyl (meth)acrylate and dialkylamine are reacted to convert into an ester adduct, the adduct is made to react with alkanolamine under the presence of a strong base nature catalyst, an amide adduct which is a synthetic intermediate is obtained after the sulfuric acid neutralizing of the ester adduct, and then thermal decomposition of the amide adduct is carried out to manufacture hydroxyalkyl (meta) acrylamide. Dibutyl amine is used for double bond protecting of methyl (meth)acrylate, and thereby thermal decomposition of the amide adduct obtained thereafter can be carried out stably without using an acid catalyst to obtain hydroxyalkyl (meth) acrylamide. COPYRIGHT: (C)2012,JPO&INPIT
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Paragraph 0019
(2016/12/12)
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- METHOD OF PRODUCING N-SUBSTITUTED (METH)ACRYLAMIDE
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PROBLEM TO BE SOLVED: To provide a method of producing N-substituted (meth)acrylamide of high purity under mild conditions. SOLUTION: This invention relates to a method of obtaining N-substituted (meth)acrylamide [3] by the detachment of an amine compound through the liquid-phase thermal decomposition of an aminopropionic acid amide derivative [1] in the presence of a catalyst mainly composed of silica, wherein R1-R5 are represented by H, a C1-32 alkyl group, and a hydroxyalkyl group. COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0053; 0057; 0058
(2018/12/12)
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- Novel amphiphilic diblock copolymers bearing acid-labile oxazolidine moieties: Synthesis, self-assembly and responsive behavior in aqueous solution
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A novel oxazolidine based acid-labile monomer N-acryloyl-2,2-dimethyl-1,3- oxazolidine (ADMO) was synthesized and polymerized by reversible addition fragmentation chain transfer (RAFT) polymerization using poly(ethylene glycol) based chain transfer agent (PEG-CTA). The diblock copolymers PEG-b-PADMO were composed of hydrophilic PEG with fixed length and hydrophobic PADMO with different lengths, which formed core-shell micelles in water. Morphologies and sizes of micelles were obtained by transmission electron microscopy (TEM) and dynamic light scattering (DLS), which showed that the shapes of polymeric aggregates developed from small spherical micelles, worm-like micelles to larger size of vesicles, as the length of PADMO increased. The hydrolysis kinetics of the micelles was studied using 1H NMR, DLS and release of loaded Nile Red dye, whose rate strongly depended on pH and micellar structure. It led to the disruption of polymeric micelles and concomitant release of the guest molecules, due to the transformation of hydrophobic PADMO into hydrophilic poly(2-hydroxyethyl acrylamide) (PHEAM).
- Cui, Qianling,Wu, Feipeng,Wang, Erjian
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scheme or table
p. 1755 - 1765
(2012/03/11)
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- Universal polymer analysis by 1H NMR using complementary trimethylsilyl end groups
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New degenerative chain transfer agents, namely 4-(trimethylsilyl)benzyl 4′-(trimethylsilyl)butane-dithioate, 4-(trimethylsilyl)benzyl 3′-(trimethylsilyl)propyl trithiocarbonate and their 3-(trimethylsilyl) benzyl isomers, that are two-fold labeled with complementary trimethylsilyl (TMS) markers, were designed and shown to be powerful tools for universal polymer analysis by conventional 1H NMR spectroscopy. Their use in controlled free radical polymerization, here the reversible addition- fragmentation chain transfer (RAFT) method, resulted in polymers with low polydispersities up to high molar masses, as well as with defined complementary TMS end groups. Thus, routine 1H NMR spectra allowed facile determination of the molar masses of polymers of various chemical structures up to at least 105 g/mol, and simultaneously provided crucial information about the content of end groups that is typically >95% when polymerizations are correctly performed. Polymerizations were carried out in various solvents for two standard monomers, namely n-butyl acrylate and styrene, as well as for two specialty monomers, so-called inimers, namely 2-(2-chloropropionyloxy)ethyl acrylate and 2-(2-chloropropionyloxy)ethyl acrylamide. The complementary end group markers revealed marked differences in the suitability of commonly used solvents for RAFT polymerization. The results demonstrate-beyond good polymerization control-that the new RAFT agents are universal, powerful tools for facile polymer analysis by routine 1H NMR spectroscopy, of their absolute molar masses as well as of the content of end groups. This is crucial information, e.g., for the synthesis of high-quality telechelics and, in particular, of block copolymers, which is difficult to obtain by other methods. Preliminary screening experiments indicate that similar uses can be envisaged for analogous ATRP systems.
- Paech, Michael,Zehm, Daniel,Lange, Maik,Dambowsky, Ina,Weiss, Jan,Laschewsky, Andre
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supporting information; experimental part
p. 8757 - 8765
(2010/08/13)
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- METHOD FOR PRODUCING CRUDE MONOMER OF HYDROXYALKYL(METH)ACRYLAMIDE
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PROBLEM TO BE SOLVED: To provide an industrially advantageous method for producing a crude hydroxyalkyl(meth)acrylamide by which the hydroxyalkyl(meth)acrylamide useful as a macromolecular coagulant usable for treatment of industrial waste water and domestic waste water, a macromolecular modifier, a pressure-sensitive adhesive, an adhesive, a synthetic raw material for a contact lens or a reactive diluent for a UV-curable resin is obtained in high purity and in high yield. SOLUTION: The method for producing the crude hydroxyalkyl(meth)acrylamide having 1% content of a norbornene derivative comprises thermally cracking the norbornene derivative in a vapor phase, condensing the formed thermally cracked gas in the vapor phase, and vaporizing the obtained condensed liquid again before distillation to remove ≥50% of cyclopentadiene in the condensed liquid. COPYRIGHT: (C)2006,JPOandNCIPI
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Page/Page column 5
(2008/06/13)
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- A novel strategy for encapsulation and release of proteins: Hydrogels and microgels with acid-labile acetal cross-linkers
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A new acid-labile acetal cross-linker was synthesized and used to prepare protein-loaded hydrogels and microgels. This cross-linker undergoes an acid-catalyzed degradation with a half-life of 5.5 min at pH 5.0 and 24 h at pH 7.4. Protein-loaded hydrogels were synthesized with this cross-linker, and their release profiles were measured as a function of pH. Hydrogels made with the acetal cross-linker release their contents in a pH-dependent manner. The acetal cross-linker was also used to synthesize microgels with sizes between 1 and 10 μm, a range suitable for phagocytosis. The unique acid sensitivity of the acetal cross-linker should make it a useful synthetic intermediate in the design of acid-sensitive drug or gene delivery systems. Copyright
- Murthy, Niren,Thng, Yi X.,Schuck, Stephany,Xu, Ming C.,Frechet, Jean M. J.
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p. 12398 - 12399
(2007/10/03)
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- Electrophoresis gels and cross-linking agents for their preparation
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Method of separating molecules by providing a cross-linked polymer gel having a cross-linking moiety of the formula wherein X, X′, Y, Z and R2 are as defined in the specification. A sample containing the molecules to be separated is placed on the gel, and the gel is subjected to a separation technique.
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- Poly(n-acryl amino acids): A new class of biologically active polyanions
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Poly(N-acryl amino acids) bearing side groups with a lipophilic character or having charged functional groups (i.e. -NH2, -COOH, -SH, -OH, and phenols) were synthesized from the radical polymerization of N-acryl amino acid monomers. Monomers were prepared from the reaction of acryloyl chloride and amino acid esters in dry solvents. Polymers of a broad molecular weight ranging from 3 000 to 60 000 Da were obtained. The polymers were optically active, and their structures were confirmed by 1H NMR and IR spectra and elemental analysis. Hydroxyl-containing polymers were sulfated in high conversion yields by SO3/pyridine complex. The newly synthesized linear homopolyanions were tested for heparin-like activities: (i) inhibition of heparanase enzyme, (ii) release of basic fibroblast growth factor (bFGF) from the extracellular matrix (ECM), and (iii) inhibition of smooth muscle cell (SMC) proliferation. Polymers based on tyrosine and leucine were highly active in all three tests (microgram level). Polymers based on phenylalanine, tert-leucine, and proline were active as heparanase inhibitors and FGF release, and polymers of trans-hydroxyproline, glycine, and serine were active only as heparanase inhibitors. The polymer of cis-hydroxyproline was inactive. It was found that a net anionic charge (i.e. carboxylic acid) is essential for biological activity. Thus, methyl ester derivatives of the active polymers, zwitterionic amino acid pendent groups (lysine, histidine), and decarboxylated amino acids (tyramine, ethanolamine) were inactive. The above active polymers did not exhibit anticoagulation activity which is considered the main limitation of heparin and heparinomimetics for clinical use. These synthetic poly(N-acryl amino acids) may have potential use in the inhibition of heparanase-mediated degradation of basement membranes associated with tumor metastasis, inflammation, and autoimmunity.
- Bentolila, Alfonso,Vlodavsky, Israel,Ishai-Michaeli, Rivka,Kovalchuk, Olga,Haloun, Christine,Domb, Abraham J.
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p. 2591 - 2600
(2007/10/03)
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- The synthesis of novel hybrid monomers
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Novel hybrid amide-ester crosslinking monomers were prepared by using methodology which utilizes the differential functionalities present within a convenient amino alcohol. Modification of the procedure to a simple one-pot reaction enables the generation of these unique monomers to be scaled to commercial levels.
- Chan, Grace Y.N.,Looney, Mark G.,Solomon, David H.,Veluayitham, Sheela
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- Deracemization process of α-aminoesters via pyridoxal. I.- Synthesis and activity of polymerizable forms of pyridoxal
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In order to immobilize pyridoxal, which is a racemization agent of α-aminoesters and could be used in an α-aminoacid deracemization process, two polymerizable analogues of this coenzyme have been synthesized.They were obtained by functionalization in the 2' or 5' position of the pyridinic ring, by a chain containing an acryloyl end group.Their catalytic activity in the homogeneous phase were evaluated in biomimetic conditions (water, pH 7, 25 deg C), was the same as in the case of pyridoxal.Keywords: racemization / α-aminoester / pyridoxal analogue / multistep synthesis / homogeneous catalysis
- Honnoraty, Anne-Marie,Mion, Louis,Collet, Helene,Teissedre, Robert,Commeyras, Auguste
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p. 709 - 720
(2007/10/02)
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