Preparation of N‐Fmoc‐Protected (S)‐5‐Amino‐4,4‐difluoro‐7‐methyloctanoic Acid,a Possible Dipeptide Isostere |
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| Authors: | Gildas Deniau Dieter Seebach |
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| Institution: | 1. Laboratorium für Organische Chemie, Departement für Chemie und Angewandte Biowissenschaften, ETH‐Zürich, H?nggerberg, Wolfgang‐Pauli‐Strasse 10, CH‐8093 Zürich, (phone: +41‐44‐632‐2990;2. fax: +41‐44‐632‐1144);3. Postdoctoral Fellow, ETH‐Zürich (2007–2009), financially supported by the Swiss National Science Foundation (Project No. 200020‐117586) and by Novartis Pharma AG. |
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| Abstract: | The title compound 1 was prepared from L ‐leucine. The key steps include a Grignard addition to Bn2‐leucinal, a CO/CF2 replacement with Et2NSF3 (DAST) and use of a Ph group as synthetic equivalent of a COOH group. The difluoro‐δ‐amino acid 1 was incorporated into a peptide 8 ; tests with various proteases showed no inhibition by this particular peptide. |
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| Keywords: | Peptides Octanoic acid (S)‐5‐amino‐4 4‐difluoro‐5‐methyl‐ CO/CF2 Replacement Homostatin mimic |
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