17929-90-7Relevant articles and documents
Isolation and characterization of racemase from Ensifer sp. 23-3 that acts on α-aminolactams and α-amino acid amides
Matsui, Daisuke,Fuhshuku, Ken-ichi,Nagamori, Shingo,Takata, Momoko,Asano, Yasuhisa
, p. 1503 - 1510 (2017)
Limited information is available on α-amino-ε-caprolactam (ACL) racemase (ACLR), a pyridoxal 5′-phosphate-dependent enzyme that acts on ACL and α-amino acid amides. In the present study, eight bacterial strains with the ability to racemize α-amino-ε-caprolactam were isolated and one of them was identified as Ensifer sp. strain 23-3. The gene for ACLR from Ensifer sp. 23-3 was cloned and expressed in Escherichia coli. The recombinant ACLR was then purified to homogeneity from the E. coli transformant harboring the ACLR gene from Ensifer sp. 23-3, and its properties were characterized. This enzyme acted not only on ACL but also on α-amino-δ-valerolactam, α-amino-ω-octalactam, α-aminobutyric acid amide, and alanine amide.
Reaction of Metal Alkoxides with Lysine: Substitution of Alkoxide Ligands vs. Lactam Formation
Metelkina, Olga,Schubert, Ulrich
, p. 1065 - 1069 (2003)
Reaction of Ti(OEt)4 with lysine results in the formation of Ti(OEt)3(lysinate), as previously reported. Contrary to that, Al(OsBu)3 only catalyzes the formation of 3-aminocaprolactam, and no substitution produc
Influence of cyclodextrin on the UCST- and LCST-Behavior of poly(2-methacrylamido-caprolactam)- Co-(N,N-dimethylacrylamide)
Burkhart, Alexander,Ritter, Helmut
, p. 1951 - 1958 (2014)
The monomer 2-methacrylamido-caprolactam (4) was synthesized from methacryloyl chloride (3) and racemic a-amino-e-caprolactam (2). Copolymerization of 4 with N,N-dimethylacrylamide (5) was carried out by a free-radical mechanism using 2,2- azobis(2-methylpropionitrile) (AIBN) as an initiator. The new copolymers show a lower critical solution temperature (LCST) in water and an upper critical solution temperature (UCST) in ethanol, 1-propanol, and 1-butanol. The solubility properties of the copolymers can be influenced significantly by the addition of randomly methylated ss-cyclodextrin (CD). The complexation of the copolymers with CD, was confirmed by the use of ROESY-NMR-spectroscopy.
Seven-membered cyclic lysine derivative monomer and preparation method thereof, and antibacterial poly(epsilon-lysine) derivative and preparation method thereof
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Paragraph 0061-0062, (2020/05/30)
The invention relates to a seven-membered cyclic lysine derivative monomer and a preparation method thereof, and an antibacterial poly(epsilon-lysine) derivative and a preparation method thereof. According to the invention, a lactam monomer is formed thro
Organocatalytic Decarboxylation of Amino Acids as a Route to Bio-based Amines and Amides
Claes, Laurens,Janssen, Michiel,De Vos, Dirk E.
, p. 4297 - 4306 (2019/08/26)
Amino acids obtained by fermentation or recovered from protein waste hydrolysates represent an excellent renewable resource for the production of bio-based chemicals. In an attempt to recycle both carbon and nitrogen, we report here on a chemocatalytic, metal-free approach for decarboxylation of amino acids, thereby providing a direct access to primary amines. In the presence of a carbonyl compound the amino acid is temporarily trapped into a Schiff base, from which the elimination of CO2 may proceed more easily. After evaluating different types of aldehydes and ketones on their activity at low catalyst loadings (≤5 mol%), isophorone was identified as powerful organocatalyst under mild conditions. After optimisation many amino acids with a neutral side chain were converted in 28–99 % yield in 2-propanol at 150 °C. When the reaction is performed in DMF, the amine is susceptible to N-formylation. This consecutive reaction is catalysed by the acidity of the amino acid reactant itself. In this way, many amino acids were efficiently transformed to the corresponding formamides in a one-pot catalytic system.
Α-amino-ε-caprolactam producing method
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Paragraph 0022-0037, (2018/08/04)
PROBLEM TO BE SOLVED: To provide a method for producing α-amino-ε-caprolactam from lysine or a salt thereof by using a nonpolar solvent which is easily recovered and recycled in place of a polar solvent such as an alcohol. SOLUTION: The problem is solved by the method for producing α-amino-ε-caprolactam, in which lysine or a salt thereof is dehydrated and cyclized in the presence of the mixed solvent of the nonpolar solvent and water kept at a temperature of 200-400°C and a pressure of 5-40 MPa. An amount of water to be used is reduced, and corrosion of a reactor is alleviated, and the nonpolar solvent is easily recovered and recycled. COPYRIGHT: (C)2012,JPO&INPIT
N,N′-(Hexane-1,6-diyl)bis(4-methyl-N-(oxiran-2-ylmethyl) benzenesulfonamide): Synthesis via cyclodextrin mediated N-alkylation in aqueous solution and further Prilezhaev epoxidation
Fischer, Julian,Millan, Simon,Ritter, Helmut
supporting information, p. 2834 - 2840 (2014/01/06)
N-alkylation of N,N′-(hexane-1,6-diyl)bis(4-methylbenzenesulfonamide) with allyl bromide and subsequent Prilezhaev reaction with m-chloroperbenzoic acid to give N,N′-(hexane-1,6-diyl)bis(4-methyl-N-(oxiran-2-ylmethyl) benzenesulfonamide) is described. Thi
Oligomeric epoxide-amine adducts based on 2-amino-N-isopropylacetamide and a-amino-ε-caprolactam: Solubility in presence of cyclodextrin and curing properties
Fischer, Julian,Ritter, Helmut
, p. 2803 - 2811 (2014/01/06)
2-Amino-N-isopropylacetamide and α-amino-ε-caprolactam were reacted with glycerol diglycidyl ether to give novel oligomeric thermoresponsive epoxide-amine adducts. These oligomers exhibit a lower critical solution temperature (LCST) behavior in water. The solubility properties were influenced with randomly methylated β-cyclodextrin (RAMEB-CD) and the curing properties of the amine-epoxide mixtures were analyzed by oscillatory rheology and differential scanning calorimetry, whereby significant differences in setting time, viscosity, and stiffness were observed.
Amino-caprolactam derivatives as γ-secretase inhibitors
Parker, Michael F.,Bronson, Joanne J.,Barten, Donna M.,Corsa, Jason A.,Du, Wengsheng,Felsenstein, Kevin M.,Guss, Valerie L.,Izzarelli, Darcy,Loo, Alice,McElhone, Kate E.,Marcin, Larry R.,Padmanabha, Ramesh,Pak, Roger,Polson, Craig T.,Toyn, Jeremy H.,Varma, Sam,Wang, Jian,Wong, Victoria,Zheng, Ming,Roberts, Susan B.
, p. 5790 - 5795 (2008/03/13)
A series of amino-caprolactam sulfonamides were developed from a screening hit. Compounds with good in vitro and in vivo γ-secretase activity are reported.
4- BROMO - 5 - (2- CHLORO - BENZOYLAMINO) - 1H - PYRAZOLE - 3 - CARBOXYLIC ACID AMIDE DERIVATIVES AND RELATED COMPOUNDS AS BRADYKININ B1 RECEPTOR ANTAGONISTS FOR THE TREATMENT OF INFLAMMATORY DISEASES
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Page 183; 143, (2008/06/13)
Disclosed are compounds of formula I and II that are bradykinin B1 receptor antagonists and are useful for treating diseases, or relieving adverse symptoms associated with disease conditions, in mammals mediated by bradykinin B1 receptor. Certain of the compounds exhibit increased potency and are also expected to exhibit increased duration of action.