title: α-Amino Acid-Isosteric α-Amino Tetrazoles.
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.
authors.affiliation: University of Groningen, Department of Drug Design, A. Deusinglaan 1, 9713 AV, Groningen, the Netherlands.
authors.forename: Ting
authors.initials: T
authors.lastname: Zhao
authors.affiliation: Faculty of Chemistry, Jagiellonian University, 3 Ingardena Street, 30-060, Kraków, Poland.
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Kurpiewska
authors.affiliation: Faculty of Chemistry, Jagiellonian University, 3 Ingardena Street, 30-060, Kraków, Poland.
authors.forename: Justyna
authors.initials: J
authors.lastname: Kalinowska-Tłuścik
authors.affiliation: Technische Universität München, Anorganisch Chemisches Institut, Garching, 85748, Germany.
authors.forename: Eberhardt
authors.initials: E
authors.lastname: Herdtweck
authors.affiliation: University of Groningen, Department of Drug Design, A. Deusinglaan 1, 9713 AV, Groningen, the Netherlands. a.s.s.domling@rug.nl.
authors.forename: Alexander
authors.initials: A
authors.lastname: Dömling
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D015195:Drug Design; D015394:Molecular Structure; D013777:Tetrazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000596:Amino Acids; D002264:Carboxylic Acids; D013777:Tetrazoles
keywords: amino acids; bioisosterism; multicomponent reactions; synthetic methods; tetrazoles
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