Disease relevance of METHYLMALEIC ACID

• The soluble fumarate reductase (FR) from Shewanella frigidimarina can catalyse the reduction of 2-methylfumarate with a k(cat) of 9.0 s(-1) and a K(M) of 32 microM [1].
• Based on the results, the mesaconate pathway is proposed to explain the (S)-glutamate fermentation process observed in Enterobacteriaceae, and 3-methylaspartase could be a marker enzyme for this pathway [2].
• Thermodynamics of the maleate and citraconate hydration reactions catalysed by malease from Pseudomonas pseudoalcaligenes [3].
• Achromobacter insolitus can be distinguished from Achromobacter spanius by its ability to grow on acetamide and to assimilate mesaconate and aconitate, and by its inability to assimilate diaminobutane [4].
• beta-methylaspartate ammonia-lyase, EC 4.3.1.2, (beta-methylaspartase) from Clostridium tetanomorphum was used to produce a 40/60 molar ratio of (2S,3R) and (2S,3S)-3-methylaspartic acids, 2a and 2b, respectively, from mesaconic acid 1 as substrate, on a large scale [5].

High impact information on METHYLMALEIC ACID

• Here, we present the structure of FR to a resolution of 1.5 A with 2-methylfumarate bound at the active site [1].
• 3-Methylaspartate ammonia-lyase as a marker enzyme of the mesaconate pathway for (S)-glutamate fermentation in Enterobacteriaceae [2].
• The pH optimum for the deamination reaction of (2S, 3S)-3-methylaspartic acid and those for the amination reaction of mesaconic acid were 9.7 and 8.5; its optimum temperature was 50 degrees C. The enzyme was stable at pH 5.5-11.0 and up to 50 degrees C. The enzyme required both divalent and monovalent cations such as Mg2+ and K+ [6].
• The enzyme preferentially acted on (2S, 3S)-3-methylaspartic acid and mesaconic acid in the deamination and the amination reactions respectively [6].
• When [14C]propionate was incubated with a cell-free extract of Rhodospirillum rubrum in the presence of glyoxylate, ATP, CoA, Mg2+, and Mn2+, radioactivity was incorporated into mesaconate (MSA) as well as into beta-methylmalate (MMA) and citramalate (CMA) [7].

Associations of METHYLMALEIC ACID with other chemical compounds

• Considering that mesaconate is an inhibitor of fumarase, the toxic effects of sodium benzoate may be attributable to the mesaconate [8].

Analytical, diagnostic and therapeutic context of METHYLMALEIC ACID

• Beta-methylaspartase-catalyzed addition of ammonia to mesaconate yielded two diastereomeric amino acids, identified by HPLC as (2S,3S)-3-methylaspartate (major product) and (2S,3R)-3-methylaspartate (minor product) [9].
• These peaks were identified by gas chromatography/mass spectrometric analyses as methylsuccinate and mesaconate [8].

References