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Substrate stereospecificity and selectivity of catechol-O-methyltransferase for DOPA, DOPA derivatives and alpha-substituted catecholamines.

Abstract：

:The substrate specificity of highly purified pig liver catechol-O-methyltransferase has been investigated kinetically. This enzyme shows stereospecificity towards the naturally occurring L-isomer of 3,4-dihydroxyphenylalanine (DOPA) which has a higher affinity and maximal velocity as a substrate than the D-form. We have confirmed the implication of the in vivo study of Ito et al. [1], that methylation of 5-S-L-cysteinyl-L-DOPA is catalysed extremely slowly by catechol-O-methyltransferase, despite the comparatively high affinity of the enzyme for the substrate. Salbutamol is not a substrate for the enzyme and DL-threo-3,4-dihydroxyphenylserine (DOPS) is such a poor substrate that accurate kinetic analysis proved impossible. Alpha-substitution of DOPA, noradrenaline and isoprenaline causes a decrease in the affinity of catechol-O-methyltransferase for these compounds. However, the "suicide' inhibitors of aromatic-L-amino acid decarboxylase (DOPA decarboxylase), fluoro- and difluoro-alpha-methyl DOPA are more superior catechol-O-methyltransferase substrates than alpha-methyl DOPA, presumably because the electron-withdrawing effect of the presence of fluorine in their structure overcomes the steric influence of the alpha-methyl group. A DOPA decarboxylase inhibitor in clinical use, benserazide, is, however, a much superior catechol-O-methyltransferase substrate and may have the therapeutic advantage of decreasing methylation of L-DOPA [2]. Alpha-Methyl dopamine has a lower Km and higher Vmax than the parent compound.

journal_name

Biochem Pharmacol

journal_title

Biochemical pharmacology

authors

Gordonsmith RH,Raxworthy MJ,Gulliver PA

doi

10.1016/0006-2952(82)90194-0

subject

Has Abstract

pub_date

1982-02-01 00:00:00

pages

433-7

issue

3

eissn

0006-2952

issn

1873-2968

pii

0006-2952(82)90194-0

journal_volume

31

pub_type

杂志文章

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