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Facing the gem ‐Dialkyl Effect in Enzyme Inhibitor Design: Preparation of Homocycloleucine‐Based Azadipeptide Nitriles
Author(s) -
Frizler Maxim,
Lohr Friederike,
Lülsdorff Michael,
Gütschow Michael
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201101350
Subject(s) - computer science , chemistry , leucine , scheme (mathematics) , combinatorial chemistry , information retrieval , stereochemistry , biochemistry , mathematics , amino acid , mathematical analysis
A tough nut to crack : In contrast to azadipeptide nitriles containing a P2 leucine residue, the synthesis of the corresponding homocycloleucine‐based inhibitors was more difficult; possibly due to the gem ‐dialkyl effect. A synthetic route to the first homocycloleucine‐derived azadipeptide nitriles as selective and highly potent cathepsin K inhibitors is presented (see scheme).