Enantiopure chiral amines synthesis using omega-transaminases is hindered by an unfavourable equilibrium, but when using isopropylamine as the amine donor the equilibrium can be completely displaced by using a specific dehydrogenase in situ for removal of formed acetone.
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Transaminase-Catalyzed Synthesis of β-Branched Noncanonical Amino Acids Driven by a Lysine Amine Donor.
J Am Chem Soc
June 2024
Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States.
Transaminases are choice biocatalysts for the synthesis of chiral primary amines, including amino acids bearing contiguous stereocenters. In this study, we employ lysine as a "smart" amine donor in transaminase-catalyzed dynamic kinetic resolution reactions to access β-branched noncanonical arylalanines. Our mechanistic investigation demonstrates that, upon transamination, the lysine-derived ketone byproduct readily cyclizes to a six-membered imine, driving the equilibrium in the desired direction and thus alleviating the need to load superstoichiometric quantities of the amine donor or deploy a multienzyme cascade.
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Chem Asian J
July 2023
Institute of Chemistry, University of Kassel, Heinrich-Plett-Str. 40, 34132, Kassel, Germany.
Ferrocene-based N-heterocyclic plumbylenes fc[(NSiMe R) Pb:] (1; fc=1,1'-ferrocenylene) are easily accessible by transamination from [(Me Si) N] Pb and the corresponding 1,1'-diaminoferrocene derivatives fc(NHSiMe R) . They may form unconventional dimers 2 by a process, which causes the cleavage of a cyclopentadienyl C-H bond and the formation of a Pb-C and an N-H bond. The monomer-dimer equilibrium (2 1⇆2) has been addressed experimentally and computationally.
View Article and Find Full Text PDFNSSN-Type Group 4 Metal Complexes in the Ring-Opening Polymerization of l-Lactide.
Inorg Chem
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Department of Chemistry and Biology, University of Salerno, via Giovanni Paolo II 132, Fisciano, Salerno I-84084, Italy.
A new class of zirconium and hafnium complexes coordinated by linear dianonic tetradentate NSSN ligands is reported. The ligands feature two amide functions coupled with two thioether groups linked by a central flexible ethane bridge and two lateral rigid phenylene bridges and differ for the substituents on the aniline nitrogen atoms, i.e.
View Article and Find Full Text PDFCrystallization and preliminary X-ray crystallographic studies of β-transaminase from Mesorhizobium sp. strain LUK.
Acta Crystallogr Sect F Struct Biol Cryst Commun
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School of Biotechnology, Yeungnam University, Gyeongsan, Republic of Korea.
β-Transaminase (β-TA) catalyzes the transamination reaction between β-aminocarboxylic acids and keto acids. This enzyme is a particularly suitable candidate for use as a biocatalyst for the asymmetric synthesis of enantiochemically pure β-amino acids for pharmaceutical purposes. The β-TA from Mesorhizobium sp.
View Article and Find Full Text PDFTransaminations with isopropyl amine: equilibrium displacement with yeast alcohol dehydrogenase coupled to in situ cofactor regeneration.
Chem Commun (Camb)
August 2010
Division of Biochemistry, School of Biotechnology, Royal Institute of Technology (KTH), AlbaNova University Centre, SE-106 91 Stockholm, Sweden.
Enantiopure chiral amines synthesis using omega-transaminases is hindered by an unfavourable equilibrium, but when using isopropylamine as the amine donor the equilibrium can be completely displaced by using a specific dehydrogenase in situ for removal of formed acetone.
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