20846-91-7Relevant articles and documents
Misumi et al.
, p. 3433,3436 (1969)
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.
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.
