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Document Figure 9 The energy profile (as calculated at the 3-21G/PM3 level [24]) for the proton transfer step A rarrow.gif B and the methyl transfer step B rarrow.gif C for catechol as a substrate. Page 351 The pK a of the catecholic hydroxyl is about 9.8. The role of the Mg 2+ ion bound to the enzyme is to make the hydroxyl groups more easily ionizable. It has been shown by quantum mechanical calculations that the hydroxyl protons can be transferred to Lys144 and Glu199 [24]. The proton transfer OH rarrow.gif Lys144 activates the hydroxyl group for the methyl transfer AdoMet rarrow.gif O -. Thus the reaction coordinate for methylation of catechols by COMT consists of a proton transfer from a hydroxyl group to Lys144 and a subsequent methyl transfer from AdoMet to the hydroxyl group (Figure 9). The Lys144 residue acts as a typical catalytic base in a general base-catalysed SN2-like nucleophilic substitution reaction [24]. IV. Inhibitors of COMT A. First-Generation Inhibitors First generation COMT inhibitors such as pyrogallol, U-0521 (3, 4-dihydroxy-2-methylpropiophenone), tropolone, and 8-hydroxyquinoline (Figure 10) were http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_351.html (1 of 2) [4/5/2004 5:28:20 PM]
Document Figure 10 Structures of some first generation COMT inhibitors: pyrogallol, U-0521 (3, 4-dihydroxy-2-methylpropiophenone), tropolone, and 8-hydroxyquinoline. Figure 11 Structures of second-generation COMT inhibitors discussed in this paper: nitecapone (OR-462), entacapone (OR-611), tolcapone (RO-40-7592), and 2-((3, 4-dihy-droxy-2-nitrophenyl) vinyl) phenylketone. http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_352.html (1 of 2) [4/5/2004 5:28:27 PM] Page 352
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Structure-based Drug Design 14 Stru
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Document 2 Structural Studies of HI
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Document 122. Marshall WS, Beaton G
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Document dine) and didanosine (dide
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Document 163. Lacey SF, Larder BA.
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Document Page 108 mulate during tre
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Document cubation of phosphotyrosin
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Document 4 Bradykinin Receptor Anta
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Document Figure 3 Previously known
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Document Table 1 Inhibition Data fo
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Document Page 166 As predicated, th
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Document References 1. Parks RE Jr.
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Document 17. Ealick SE, Rule SA, Ca
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Document 6 Structural Implications
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Document Page 176 0.43 Å) as the c
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Document III. Results and Discussio
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Document Page 202 269, and valine-2
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Page 415 and 416: Document 17. Szelke M. Chemistry of
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Page 421 and 422: Document Page 343 14 Structural Asp
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Document Page 629 ML, Clare M, Decr
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Document D ddI, 152 tumour necrosis
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Document antistasin peptides, 281 c
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Document Phosphoglycerate kinase (P
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Document [Protease targets] serinyl
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