Investigation of the synthetic route to pepstatin analogues by SPPS using O‐protected and O‐unprotected statine as building blocks |
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Authors: | Cosimo D Cadicamo Vivian Asante Morhaf Abu Ammar Claudia Borelli Hans C Korting Beate Koksch |
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Institution: | 1. Department of Organic Chemistry, FU Berlin, Takustra?e 3, D‐14195 Berlin, Germany;2. Departement of Dermatology and Allergy, Ludwig Maximilian University of Munich, Frauenlobstra?e 9‐11, D‐80337 Munich, Germany |
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Abstract: | The synthetic route to pepstatin derivatives by a solid phase peptide synthesis using either O‐protected or O‐unprotected statine as a building block has been investigated. Statine was prepared according to a modified literature procedure, whereas protection of its 3‐hydroxyl moiety using tert‐butyldimethylsilylchloride (TBSCl) provided the novel O‐TBS‐protected statine building block. The O‐tert‐butyldimethylsilyl (TBS)‐protected statine approach provides an improved synthetic strategy for the preparation of statine‐containing peptides as demonstrated by the synthesis of the pepstatin analogue iva‐Val‐Leu‐Sta‐Ala‐Sta. Copyright © 2009 European Peptide Society and John Wiley & Sons, Ltd. |
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Keywords: | pepstatin A O‐silylation SPPS N‐Fmoc‐O‐TBS‐statine |
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