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Document This led to the design and syntheses of 4-amino-Neu5Ac2en and 4-guanidino-Neu4Ac2en [91] which bound to A/Tokyo/3/67 with a K i of 50 nM and 0.2 http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_475.html (2 of 2) [4/9/2004 12:25:17 AM]
Document Page 476 nM, respectively. These compounds were later shown <strong>by</strong> x-ray studies of 4-guanidino and 4-amino- Neu4Ac2en complexed with A/Tokyo/3/67 neuraminidase to bind close to that predicted <strong>by</strong> the design studies. However details of the interactions of the guanidinyl group of the 4-guanidino-Neu4Ac2en with the glutamic acid groups (Glu119 and Glu277) in the floor of the active site were slightly different. This was confirmed on a higher resolution x-ray study (Figure 9) of a 4-guanidino-Neu4Ac2en complexed with Tern N9 neuraminidase [72]. One of the primary guanidinyl nitrogens of 4-guanidino-Neu4Ac2en is hydrogen bonded to the main-chain oxygen at residue 178, a carboxylate oxygen of Glu227, and a water molecule. The other primary guanidinyl nitrogen interacts with the main-chain oxygen of residues 178 and 151. The secondary guanidinyl nitrogen interacts with the carboxylate of Glu119 and Asp151. The interactions with Glu119 are electrostatic and van der Waals in character and lack hydrogenbonding geometry (postulated in the design study) as the carboxylate group of Glu119 stacks parallel to the guanidinyl group. Furthermore, theoretical energy-minimized structures of the complex using AMBER [92] converged to the x-ray structure only if the protein nonhydrogen atoms were kept rigid in the x-ray structure [72]. Otherwise this resulted in active site residues showing large distortions in their conformation. This is an example of the difficulty in correctly modeling even modest changes in the interactions of an inhibitor/active site complex. The 4-guanidino analog shows potent inhibition of neuraminidase activity in all known wild strains of influenza. Furthermore it is very specific to in- Figure 9 Stereo image of the Tern/N9 4-guanidino-Neu5Ac2en complex showing the hydrogen-bond interactions (dotted lines) of the inhibitor with conserved residues in the active site of the enzyme. Nitrogen, oxygen, and carbon atoms are shaded black, dark gray, and light gray, respectively. http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_476.html [4/9/2004 12:26:21 AM]
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Structure-based Drug Design 14 Stru
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Document [Protease targets] serinyl
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