Facing the  gem ‐Dialkyl Effect in Enzyme Inhibitor Design: Preparation of Homocycloleucine‐Based Azadipeptide Nitriles | Zendy

Frizler Maxim | Zendy; Lohr Friederike | Zendy; Lülsdorff Michael | Zendy; Gütschow Michael | Zendy

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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).

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