1.1.99.31: (S)-mandelate dehydrogenase

This is an abbreviated version!
For detailed information about (S)-mandelate dehydrogenase, go to the full flat file.

Word Map on EC 1.1.99.31

Reaction

(S)-Mandelate
+
acceptor
=
phenylglyoxylate
+
reduced acceptor

Synonyms

(S)-mandelate dehydrogenase, L-mandelate dehydrogenase, L-MDH, MDH, SManDH, SMDH

ECTree

     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.99 With unknown physiological acceptors
                1.1.99.31 (S)-mandelate dehydrogenase

Systematic Name

Systematic Name on EC 1.1.99.31 - (S)-mandelate dehydrogenase

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SYSTEMATIC NAME
IUBMB Comments
(S)-2-hydroxy-2-phenylacetate:acceptor 2-oxidoreductase
This enzyme is a member of the FMN-dependent alpha-hydroxy-acid oxidase/dehydrogenase family [1]. While all enzymes of this family oxidize the (S)-enantiomer of an alpha-hydroxy acid to an alpha-oxo acid, the ultimate oxidant (oxygen, intramolecular heme or some other acceptor) depends on the particular enzyme. This enzyme transfers the electron pair from FMNH2 to a component of the electron transport chain, most probably ubiquinone [1,2]. It is part of a metabolic pathway in Pseudomonads that allows these organisms to utilize mandelic acid, derivatized from the common soil metabolite amygdalin, as the sole source of carbon and energy [2]. The enzyme has a large active-site pocket and preferentially binds substrates with longer sidechains, e.g. 2-hydroxyoctanoate rather than 2-hydroxybutyrate [1]. It also prefers substrates that, like (S)-mandelate, have beta unsaturation, e.g. (indol-3-yl)glycolate compared with (indol-3-yl)lactate [1]. Esters of mandelate, such as methyl (S)-mandelate, are also substrates [3].