6064-63-7Relevant articles and documents
Catalytic performance of a supramolecular bienzyme complex formed with artificial aminotransferase and natural lactate dehydrogenase
Kikuchi, Jun-Ichi,Kamijyo, Yasuyuki,Etoh, Hiroshi,Murakami, Yukito
, p. 427 - 428 (1996)
A supramolecular bienzyme complex was constituted in a combination of a catalytic bilayer membrane as an artificial aminotransferase with a natural lactate dehydrogenase and the resulting cooperative system enhanced the catalytic activity of the artificial enzyme to promote a sequential transformation of α-amino acids to the corresponding α-hydroxy acids via formation of α-keto acids, exhibiting a marked substrate specificity.
Takeuchi,Yonehara
, p. 5197 (1966)
Synthesis of Dicarboxylic Acids from Aqueous Solutions of Diols with Hydrogen Evolution Catalyzed by an Iridium Complex
Fujita, Ken-ichi,Toyooka, Genki
, (2020/07/13)
A catalytic system for the synthesis of dicarboxylic acids from aqueous solutions of diols accompanied by the evolution of hydrogen was developed. An iridium complex bearing a functional bipyridonate ligand with N,N-dimethylamino substituents exhibited a high catalytic performance for this type of dehydrogenative reaction. For example, adipic acid was synthesized from an aqueous solution of 1,6-hexanediol in 97 % yield accompanied by the evolution of four equivalents of hydrogen by the present catalytic system. It should be noted that the simultaneous production of industrially important dicarboxylic acids and hydrogen, which is useful as an energy carrier, was achieved. In addition, the selective dehydrogenative oxidation of vicinal diols to give α-hydroxycarboxylic acids was also accomplished.
(2R)- and (2S)- 2-hydroxy- hexanoyl and octanoyl-L-homoserine lactones: New highly potent Quorum Sensing modulators with opposite activities
Jeanneau, Erwann,Queneau, Yves,Soulère, Laurent,Zhang, Qiang
supporting information, (2020/10/12)
The synthesis and the QS modulation activity of diastereoisomerically pure 2-hydroxy-N-acyl-L-homoserine lactones (2-OH-AHLs) are unveiled. (2R)- and (2S)- 2-hydroxy-N-hexanoyl-L-homoserine lactone and 2-hydroxy-N-octanoyl-L-homoserine lactone have been identified as very potent QS agonists and antagonists on the Vibrio fischeri-quorum sensing system with opposite activities depending on the configuration of the carbon atom with the hydroxyl group. Flexible molecular docking showed that the (2R)–OH configuration in the antagonist isomer induces new hydrogen bonds with Tyr70 and Asp79, two importantly conserved residues in the LuxR protein family, while the (2S)–OH agonist configuration exhibits a binding mode comparable to the natural ligand 3-oxo-hexanoyl-L-homoserine lactone (OHHL). For the analogs with long alkyl chain 3a and 3b and aromatic analogs, all are antagonists with no effect of the configuration at C-2.
Preparative Asymmetric Synthesis of Canonical and Non-canonical a-amino Acids through Formal Enantioselective Biocatalytic Amination of Carboxylic Acids
Dennig, Alexander,Blaschke, Fabio,Gandomkar, Somayyeh,Tassano, Erika,Nidetzky, Bernd
supporting information, p. 1348 - 1358 (2019/10/28)
Chemical and biocatalytic synthesis of non-canonical a-amino acids (ncAAs) from renewable feedstocks and using mild reaction conditions has not efficiently been solved. Here, we show the development of a three-step, scalable and modular one-pot biocascade for linear conversion of renewable fatty acids (FAs) into enantiopure l-a-amino acids. In module 1, selective a-hydroxylation of FAs is catalyzed by the P450 peroxygenase P450CLA. By using an automated H2O2 supplementation system, efficient conversion (46 to >99%; TTN>3300) of a broad range of FAs (C6:0 to C16:0) into valuable a-hydroxy acids (a-HAs; >90% a-selective) is shown on preparative scale (up to 2.3 gL1 isolated product). In module 2, a redox-neutral hydrogen borrowing cascade (alcohol dehydrogenase/amino acid dehydrogenase) allowed further conversion of a-HAs into l-a-AAs (20 to 99%). Enantiopure l-a-AAs (e.e. >99%) including the pharma synthon l-homo-phenylalanine can be obtained at product titers of up to 2.5 gL1. Based on renewables and excellent atom economy, this biocascade is among the shortest and greenest synthetic routes to structurally diverse and industrially relevant ncAAs.
