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Document Active Site The active site of COMT consists of the AdoMet binding domain and the catalytic site. The structural elements and individual interactions between COMT residues and the enzymatic-action-participating ligands are demonstrated in detail in Figures 5 to 8. Page 349 AdoMet Binding by COMT. The active-site residues, which have significant interactions with the coenzyme, are shown in Figure 6. The loop region between strand β1 and helix α4 forms the AdoMetbinding consensus sequence (in COMT GAxxG) that is conserved in methyltransferases [23]. In this region the terminal amino and carboxyl groups of AdoMet are bound. The last residue of the strand β2, Glu90, forms a hydrogen bond to the ribose hydroxyls. The residue Met91 has face-to-face van der Waals contacts on one side, and His142 has edge-to-face contacts on the opposite side of the adenine ring. The residue Trp143 closes the adenine of AdoMet into the protein with face-to-edge contact. Furthermore, the N-6 atom of the adenine hydrogen binds to Ser119. The Met40 residue holds the sulphur of AdoMet with the methyl group in right position towards the hydroxyl group of the catechol substrate. As a result of the various hydrogen bonds and van der Waals contacts, AdoMet has a high affinity to COMT with a dissociation constant of 23 μM [19]. Catalytic Site. The catalytic site of COMT is a rather simple environment formed by the metal ion and by the amino acids important for substrate binding and catalysis of the methylation reaction. The magnesium ion plays a crucial role for the catalytic activity of COMT. Figure 7 shows the binding of magnesium to COMT as derived from the Figure 7 Magnesium binding in COMT. The magnesium ligands are Asp141, Asp169, Asn170, both hydroxyls of 3, 5-dinitrocatechol (DNC) and a water molecule (W). http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_349.html (1 of 2) [4/5/2004 5:28:09 PM]
Document Figure 8 The catalytic machinery of COMT. Shown are the COMT residues important for catalysis, Mg 2+ binding, the catechol as substrate, and the methyl-donating coenzyme AdoMet. The hydrophobic walls are defined by two tryptophane residues and a proline residue. Page 350 crystallographic studies. Magnesium has an octahedral coordination to two aspartic acid residues (Asp141 and Asp169), to an asparagine residue (Asn170), to both catechol hydroxyls of the substrate, and to a water molecule. In addition to the Mg 2+ ion, Lys144 and Glu199 participate directly in the methylation reaction as shown in Figure 8. The “gate keeper” residues Trp38 and Pro174 form the hydrophobic “walls” and define the selectivity of the enzyme to different side chains of the substrate. They play a significant role in the binding of the substrates and inhibitors of COMT [19, 21]. III. Mechanism of the Catalytic Action of COMT The catalytic site is a shallow groove with the catalytic machinery at the bottom as illustrated in Figure 8. The two hydroxyl oxygens of a catechol substrate bind directly to the Mg 2+ ion. The active methyl group of AdoMet is near one of the hydroxyl groups, on one side of the catechol ring. The amino group of Lys144 is also located near this hydroxyl group, on the other side of the catechol ring from AdoMet. The Glu199 residue is near the other hydroxyl group. http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_350.html [4/5/2004 5:28:14 PM]
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Document Page 108 mulate during tre
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Document when metals are bound. Fin
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