Angewandte Chemie - International Edition p. 314 - 318 (2011)
Update date:2022-09-26
Topics:
Hardegger, Leo A.
Kuhn, Bernd
Spinnler, Beat
Anselm, Lilli
Ecabert, Robert
Stihle, Martine
Gsell, Bernard
Thoma, Ralf
Diez, Joachim
Benz, Joerg
Plancher, Jean-Marc
Hartmann, Guido
Banner, David W.
Haap, Wolfgang
Diederich, Francois
Halogen bonding triggers activity: Increasing binding affinity was observed for a series of covalent human Cathepsin L inhibitors by exchanging an aryl ring H atom with Cl, Br, and I, which undergo halogen bonding with the C=O group of Gly61 in the S3 pocket of the enzyme. Fluorine, in contrast, strongly avoids halogen bonding (see scheme). The strong distance and angle dependence of halogen bonding was confirmed for biological systems. Copyright
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