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Orthogonally Protected Thiazole and Isoxazole Diamino Acids: An Efficient Synthetic Route
Author(s) -
Butler Jeffrey D.,
Coffman Keith C.,
Ziebart Kristin T.,
Toney Michael D.,
Kurth Mark J.
Publication year - 2010
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.201001492
Subject(s) - thiazole , isoxazole , amino acid , chemistry , scheme (mathematics) , combinatorial chemistry , stereochemistry , atp synthase , potency , computer science , computational biology , biochemistry , biology , mathematics , in vitro , enzyme , mathematical analysis
An efficient strategy has been developed for the synthesis of heteroaromatic amino acids (HAAs). These methods generate mono‐ or orthogonally protected diamino acids from β‐amino acids (see scheme). Their synthetic reliability and biological potential was demonstrated through the synthesis of an anthranilate synthase (AS) and isochorismate synthase (IS) inhibitor with improved potency.