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
ASYMMETRIC CATALYTIC SYNTHESIS OF LYSINE BY HYDROGENATION OF α-NITROCAPROLACTAM
Klabunovskii, E. I.,Gogoladze, D. D.,Levitina, E. S.,Karpeiskaya, E. I.,Godunova, L. F.,et al.
, p. 1475 - 1478 (1987)
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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.
