α‐Amino Acid‐Isosteric α‐Amino Tetrazoles |
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| Authors: | Ting Zhao Katarzyna Kurpiewska Justyna Kalinowska‐Tłuścik Eberhardt Herdtweck Prof. Dr. Alexander Dömling |
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| Affiliation: | 1. University of Groningen, Department of Drug Design, Groningen, the Netherlands;2. Faculty of Chemistry, Jagiellonian University, Kraków, Poland;3. Technische Universit?t München, Anorganisch Chemisches Institut, Garching, Germany;4. http://www.drugdesign.nl/ |
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| Abstract: | The synthesis of all 20 common natural proteinogenic and 4 otherα‐amino acid‐isosteric α‐amino tetrazoles has been accomplished, whereby the carboxyl group is replaced by the isosteric 5‐tetrazolyl group. The short process involves the use of the key Ugi tetrazole reaction followed by deprotection chemistries. The tetrazole group is bioisosteric to the carboxylic acid and is widely used in medicinal chemistry and drug design. Surprisingly, several of the common α‐amino acid‐isosteric α‐amino tetrazoles are unknown up to now. Therefore a rapid synthetic access to this compound class and non‐natural derivatives is of high interest to advance the field. |
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| Keywords: | amino acids bioisosterism multicomponent reactions synthetic methods tetrazoles |
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