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498-94-2Relevant articles and documents
Electrocatalytic synthesis of isonipecotic acid
Osadchenko,Tomilov
, p. 499 - 500 (2006)
An electrocatalytic synthesis of isonipecotic acid was carried out by cathodic reduction of isonicotinic acid in a membrane electrolyzer on a copper cathode activated with Raney nickel in an alkaline medium under mild conditions. Pleiades Publishing, Inc., 2006.
Preparation method N-Boc-4 -piperidinecarboxylic acid
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Paragraph 0012; 0031-0037, (2021/11/06)
The invention discloses a preparation method of N-Boc-4 - piperidinecarboxylic acid, which comprises the following steps: adding 4 - piperidine formic acid into ethanol, dropwise adding Boc anhydride at room temperature, stirring the reaction to the solution, continuing to react at room temperature to a dot plate without raw materials. The solvent is evaporated till the system is in a viscous state and then stopped, added with water and then filtered to dry the filter cake. Wherein, 4 - piperidinecarboxylic acid, Boc anhydride and ethanol mass ratio 100:169 - 185:450 - 550.4 - piperidinecarboxylic acid is prepared by carrying out enzymatic hydrolysis on 4 - cyanopyridine to obtain pyridine -4 - formic acid. High pressure hydrogenation of pyridine -4 - formic acid to give 4 - piperidinecarboxylic acid.
High-efficiency synthesis method of methyl 4-piperidineacetate
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Paragraph 0030; 0040; 0046; 0050; 0051; 0060; 0070, (2019/01/14)
The invention discloses a high-efficiency synthesis method of methyl 4-piperidineacetate. The high-efficiency synthesis method comprises the following steps: firstly, preparing a colloid; secondly, taking titanium tetrachloride, di-n-octyl ether, cetylamine and carbon disulfide as raw materials to prepare reaction liquid; adding the reaction liquid into the colloid and dropwise adding ammonia water for precipitating to prepare a catalyst; taking 4-picolinic acid as a raw material and preparing 4-nipecotic acid under the reaction of the catalyst; taking the 4-nipecotic acid as the raw materialto prepare the methyl 4-piperidineacetate. The method has the advantages of simple operation, low preparation cost, high yield of a target product and easiness in separation.
Characterization of an enantioselective amidase from Cupriavidus sp. KNK-J915 (FERM BP-10739) useful for enzymatic resolution of racemic 3-piperidinecarboxamide
Nojiri, Masutoshi,Taoka, Naoaki,Yasohara, Yoshihiko
, p. 136 - 142 (2014/12/10)
A novel amidase (CsAM) acting on (R,S)-N-benzyl-3-piperidinecarboxamide was purified from Cupriavidus sp. KNK-J915 (FERM BP-10739) and characterized. The enzyme acts on (R,S)-N-benzyl-3-piperidinecarboxamide S-selectively to yield (R)-N-benzyl-3-piperidinecarboxamide. Analytical gel filtration column chromatography and SDS-PAGE revealed that the enzyme is a tetramer with a subunit of approximately 47 kDa. It has a broad substrate spectrum against nitrogen-containing heterocyclic amides. Its optimal pH and temperature are 8.0-9.0 and 50 °C, respectively. The CsAM gene was cloned and sequenced, and it was found to comprise 1341 bp and encode a polypeptide of 46,388 Da. The deduced amino acid sequence exhibited 78% identity to that of a putative amidase (CnAM) from Cupriavidus necator JMP134. The cultured cells of recombinant Escherichia coli producing CnAM could be used for the S-selective hydrolysis of (R,S)-N-benzyl-3-piperidinecarboxamide but could not be used for the S-selective hydrolysis of (R,S)-3-piperidinecarboxamide because of its very low level of selectivity. In contrast, the cultured cells of recombinant E. coli producing CsAM could hydrolyze both (R,S)-N-benzyl-3-piperidinecarboxamide and (R,S)-3-piperidinecarboxamide with high S-selectivity.
Use of Functionalized Onium Salts for Peptide Synthesis
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, (2010/12/18)
A subject of the invention is the use of a salt with a dedicated task of formula (I): [in-line-formulae]A+-L-R—OY, X?[/in-line-formulae] as soluble support for peptide synthesis, in which: X? represents a functional or non-functional anion,Y represents either a hydrogen atom, or a —COOR1 group, R1 representing in particular an alkyl group comprising 1 to 20 carbon atoms,A+ represents a cationic entity,L represents an arm, in particular an alkyl group of 3 to 20 carbon atoms,R represents in particular a group of formula —C(Ra)(Rb)—, Ra and Rb representing independently of one another in particular a hydrogen or an alkyl group, comprising 1 to 20 carbon atoms.
Novel betaines of the hexaalkylguanidinio-carboxylate type
Walter, Matthias,Maas, Gerhard
experimental part, p. 1617 - 1624 (2010/06/22)
Betaines 7a, b and 8a, b have been prepared from 3- and 4-piperidinecarboxylic acid and N,N,N′N′-tetraalkyl- chloroformamidinium chlorides via the corresponding methyl esters. These betaines are highly hygroscopic, thermally very stable, and, with the exception of 7b, have rather low melting points. They undergo a surprisingly facile alkaline cleavage of the hexaalkylguanidinium moiety. They react with dichloromethane by a twofold nucleophilic substitution to form methylene dicarboxylates such as 11. The NMR (1H, 13C) data of betaines 7 and 8 are discussed.
Anti-heparin peptides
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, (2008/06/13)
The invention concerns a compound exhibiting an anti-heparin activity, of formula Z Bm ! (AXA)x Bn ! (AXA)y Bo (AXA)z Bp, the diagnostic reagents comprising it and the use of said compound in an in vitro diagnostic test of a medicine for anti-heparin activity.
Solid phase supports
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, (2008/06/13)
Embodiments of the present invention generally relate to carrying out organic chemistry on solid supports comprising derivatised functionalities, methods for synthesizing said supports, methods for synthesizing compounds comprising amine groups or N-containing heterocycles using said solid supports, intermediate compounds linked to said supports and uses thereof.
Polymerization- and solvent-triggered cooperativity between copper(II) ions in the catalysis of the hydrolysis of amino esters by pyridine-based ligands
Scrimin, Paolo,Tecilla, Paolo,Tonellato, Umberto
, p. 1143 - 1153 (2007/10/03)
Polymeric (2) and oligomeric (4, 5) materials made of repeating units of 2,6-diaminomethylpyridine and 4,4′-diphenylmethane have been synthesized with the number of monomeric units (n) ranging from 2 to 29. In 1:1 DMSO/water solutions, these materials are fully soluble and strongly bind CuII ions. The complexes catalyze to different extents the hydrolysis of the p-nitrophenyl esters of α-, β-, and γ-amino acids. Only CuII complexes of polymeric 2 (n ≥ 10) are more effective catalysts than free CuII ions in the cleavage of β-amino esters. Such enhanced reactivity, which in the case of β-alanine p-nitrophenyl ester (β-AlaPNP) amounts to almost two orders of magnitude when the comparison is made with the CuII complex of monomeric ligand (N,N'-benzyl)-2,6-aminomethylpyridine (3), is observed in 1:1 (v/v) DMSO/H2O only when a certain degree of polymerization is reached (6 3CH2OH/H2O the kinetic benefits of the complexes of polymer 2 (n = 10) diminishes and vanishes in 9:1 (v/v) CH3CH2OH/H2O. Analysis of rate data suggests that two neighboring CuII ions bound to the polymeric ligands cooperate for the occurrence of the hydrolytic process: one of them coordinates the amino group of the substrate so that the carbonyl of the carboxylate faces the second metal ion which delivers a bound hydroxyl acting as the nucleophilic species. The selectivity toward β-amino ester is likely associated with a rather rigid conformation of these metallopolymers which places two metal centers at the appropriate distance one from the other. It is suggested that the onset of the metal ion cooperativity is connected to a conformational change of the metallopolymer from an extended to a globular structure, likely triggered by hydrophobic forces.