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Document Page 336 P 1' in human and mouse angiotensinogens. Accordingly residue 213 is leucine in human renin and valine in mouse renin. The S 1' pockets of chymosin, pepsin, and endothiapepsin have an aromatic side chain at residue 189 while the renins have amino acids with smaller side chains (valine in human and serine in mouse renins). This would be expected to make the pocket larger in renins. However the structure of the mouse renin complex shows that the substrate moves closer to the enzyme in renins as a result of the smaller residue at 189 and the pocket is made even more compact due to a compensatory change in the position and composition of the polyproline loop (residues 290–297). Thus, the specificity difference at this site arises not only from a compensatory movement of a secondary structure, in this case a loop region, but also from the substitution of an enzyme residue that allows the substrate to come closer to the body of the enzyme. Elaboration of loops on the periphery of the binding cleft in renins also influences the specificity. This is most marked at P 3' and P 4', for which it has been particularly difficult to obtain complexes with welldefined conformations for other aspartic proteinases. In endothiapepsin, which has been the subject of the greatest number of studies, different conformations are adopted at P 3' and the residue at P 4' is generally disordered. In contrast these residues are clearly defined in mouse renin. This is mainly a consequence of the polyproline loop, illustrated in Figure 6, which occurs uniquely in renins. The x-ray analysis of the mouse renin complex shows that the S 3' and S 4' subsites are formed by the polyproline loop together with residues of the flap, and a similar situation is likely to occur in human renin. The welldefined interactions of P 3' described in the mouse renin complex explains the significant affinity when inhibitors have phenylalanine or tyrosine at P 3' as well as the importance of a P 3' residue for catalytic cleavage of a substrate by renin [50]. Hydrogen bonds between the side chains of the inhibitor and the enzyme do not play a major role in most specificity pockets. However, S 2 is an exception. This subsite is large and contiguous with S 1', so that in human renin the S-methyl cysteine (SMC) side chain of P 2 is oriented towards the S 1' pocket, which is only partly filled by the isopropyloxy group of the putative P 1' residue. The carbonyl oxygen of P 2 accepts a hydrogen from the O γ of Ser76, which is unique to human renin; residue 76 is a highly conserved glycine in all the other aspartic proteinases, including mouse renin. In mouse renin the P 2 histidyl group has a different orientation and forms a hydrogen bond with the O γ of Ser222. If such a conformation were adopted by the human angiotensinogen in complex with human renin, the two imidazole nitrogens would be hydrogen bonded to the O γ of both Ser76 and Ser222. The observed reduction in the rate of cleavage of a human angiotensinogen analog containing a 3-methyl histidine substituent at P 2 [51] could be explained on the basis of the hydrogen bonding scheme proposed above. http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_336.html [4/5/2004 5:26:17 PM]
Document IV. Rational Drug Design Figure 6 The P 3' tyrosine residue of the mouse renin inhibitor complex showing the unique polyproline loop on the right. Specificity of this and neighboring subsites in renins must derive partly from this rigid loop region. Page 337 The pioneering work of Burton, Szelke, and others in developing peptide-based renin inhibitors has been followed by a worldwide commercial effort to elaborate such compounds into therapeutically active antihypertensives. The twin problems of insufficient oral bioavailability and rapid clearance has seemingly presented major obstacles to success. In addition, the possible advantages of renin inhibitors compared with ACE inhibitors remain questionable. Never-theless information from human-renin crystallographic studies—such as the more recent high resolution analyses [52] and algorithms for analysing voids in the complexes as potential sites for elaborating the drug molecule (e.g. Figure 7)—may yet provide leads for compounds with suitable therapeutic characteristics. The detailed analyses of renin-inhibitor complexes reported here confirm the general structural features thought to contribute to renin's specificity but http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_337.html (1 of 2) [4/5/2004 5:26:24 PM]
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Document Table 1 Approval Indicatio
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Document Cyclotheonamide A (CtA), 2
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Document D ddI, 152 tumour necrosis
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Document antistasin peptides, 281 c
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