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α‐Amino Acid‐Isosteric α‐Amino Tetrazoles
Author(s) -
Zhao Ting,
Kurpiewska Katarzyna,
KalinowskaTłuścik Justyna,
Herdtweck Eberhardt,
Dömling Alexander
Publication year - 2016
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.201504520
Subject(s) - tetrazole , chemistry , amino acid , stereochemistry , carboxylic acid , combinatorial chemistry , organic chemistry , biochemistry
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.