52759-67-8Relevant academic research and scientific papers
Production of (S,S)-ethylenediamine-N,N′-disuccinic acid from ethylenediamine and fumaric acid by bacteria
Takahashi, Rikiya,Yamayoshi, Kenji,Fujimoto, Naoshi,Suzuki, Masaharu
, p. 1269 - 1273 (1999)
We tried to produce (S,S)-ethylenediamine-N,N′-disuccinic acid [(S,S)-EDDS] with the aid of microorganisms that can degrade the compound. A reaction mixture consisting of ethylenediamine and fumaric acid was incubated with the bacteria isolated from soil and sludge, and we found that several kinds of bacteria such as Sphingomonas, Brevundimonas, Pseudomonas, and Acidovorax produced (S,S)-EDDS. The optimum pH and the temperature for the production was pH 7.5 and 35°C for Acidovorax sp. TNT149 and the bacterial cells produced 90 mmoles of (S,S)-EDDS from 200 mmoles of ethylenediamine and 350 mmoles of fumaric acid under these reaction condition.
Structural Basis for the Catalytic Mechanism of Ethylenediamine- N, N′-disuccinic Acid Lyase, a Carbon-Nitrogen Bond-Forming Enzyme with a Broad Substrate Scope
Poddar, Harshwardhan,De Villiers, Jandré,Zhang, Jielin,Puthan Veetil, Vinod,Raj, Hans,Thunnissen, Andy-Mark W. H.,Poelarends, Gerrit J.
, p. 3752 - 3763 (2018/05/23)
The natural aminocarboxylic acid product ethylenediamine-N,N′-disuccinic acid [(S,S)-EDDS] is able to form a stable complex with metal ions, making it an attractive biodegradable alternative for the synthetic metal chelator ethylenediaminetetraacetic acid (EDTA), which is currently used on a large scale in numerous applications. Previous studies have demonstrated that biodegradation of (S,S)-EDDS may be initiated by an EDDS lyase, converting (S,S)-EDDS via the intermediate N-(2-aminoethyl)aspartic acid (AEAA) into ethylenediamine and two molecules of fumarate. However, current knowledge of this enzyme is limited because of the absence of structural data. Here, we describe the identification and characterization of an EDDS lyase from Chelativorans sp. BNC1, which has a broad substrate scope, accepting various mono- and diamines for addition to fumarate. We report crystal structures of the enzyme in an unliganded state and in complex with formate, succinate, fumarate, AEAA, and (S,S)-EDDS. The structures reveal a tertiary and quaternary fold that is characteristic of the aspartase/fumarase superfamily and support a mechanism that involves general base-catalyzed, sequential two-step deamination of (S,S)-EDDS. This work broadens our understanding of mechanistic diversity within the aspartase/fumarase superfamily and will aid in the optimization of EDDS lyase for asymmetric synthesis of valuable (metal-chelating) aminocarboxylic acids.
Novel Acid Dianhydride, Mehtod for Preparing the Same and Polyimides Prepared from the Same
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Paragraph 0074-0077, (2017/01/09)
The present invention relates to a novel acid dianhydride, a method for preparing the same, and a polyimide prepared therefrom. More specifically, the acid dianhydride according to the present invention is useful as a colorless transparent polyimide unit exhibiting excellent thermal stability and a low dielectric ratio, and the polyimide of the present invention has excellent solubility to an organic solvent compared with the conventional polyimide.
Diester amine adducts
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Page column 8-9, (2008/06/13)
Described are diester amine adducts of formula (1) wherein R1, R2, R3, R4are each independently of one another C4-C22alkyl; C2-C22alkenyl; or C5-C7cycloalkyl; X1and X2are each independently of the other hydrogen, C1-C4alkyl; C2-C4hydroxyalkyl or C2-C4hydroxyhaloalkyl; Y is a radical of formula (1b); A1is C2-C3alkylene or 2-hydroxy-n-propylene; X3is hydrogen; C1-C4alkyl, C2-C4hydroxyalkyl; or C2-C4hydroxyhaloalkyl; (A) is an asymmetrical carbon atom in the R- or S-configuration, wherein, if C1=R, C2=R; C1=S, C2=S; and C1=R; C2=S; m1is 1 or 2; and n is an integer from 1 to 4; p is 0 or 1; which adducts may be in the form of free bases or ammonium salts. Said compounds are precursors of compounds having good complex-forming properties and are thus able to effectively bind heavy metal ions such as iron, zinc, magnesium or copper ions and to prevent metal-initiated oxidations after enzymatic or chemical cleavage. They have a plurality of uses, for example in foods, beverages, derusting and decalcification baths, as additives in liquids for cooling-water circuits, in personal-care products, as bleaching stabilizers, in cleaning agents and detergents, in the textile industry and also as soft handle agents for organic fibre materials.
Asymmetric synthesis of new chiral europium N,N'-disuccinate complexes: Shift reagents for aqueous solutions and application in the enantiomeric excess determination of amino acids
Hulst,De Vries,Feringa
, p. 7453 - 7458 (2007/10/02)
The synthesis of new chiral N,N'-disuccinate ligands (R,R)-8, (R,R)-9, and (S,S)-10 from (5R)- or (5S)-(menthyloxy)-2(5H)-furanone is described. These ligands, after complexation with EuCl3·6H2O, are highly suitable as chiral shift reagents for the enantiomeric excess determination of amino acids and α-alkylated amino acids in aqueous solutions. Resolution experiments using various amino acids and their derivatives and a study of the pH dependency of the induced diastereomeric shift differences are included.
