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Helical Oligomers of Thiazole‐Based γ‐Amino Acids: Synthesis and Structural Studies
Author(s) -
Mathieu Loïc,
Legrand Baptiste,
Deng Cheng,
Vezenkov Lubomir,
Wenger Emmanuel,
Didierjean Claude,
Amblard Muriel,
AverlantPetit MarieChristine,
Masurier Nicolas,
Lisowski Vincent,
Martinez Jean,
Maillard Ludovic T.
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201302106
Subject(s) - thiazole , aqueous solution , solid state , amino acid , helix (gastropod) , chemistry , nuclear magnetic resonance spectroscopy , combinatorial chemistry , stereochemistry , crystallography , organic chemistry , biochemistry , biology , ecology , snail
9‐Helix : 4‐Amino(methyl)‐1,3‐thiazole‐5‐carboxylic acids (ATCs) were synthesized as new γ‐amino acid building blocks. The structures of various ATC oligomers were analyzed in solution by CD and NMR spectroscopy and in the solid state by X‐ray crystallography. The ATC sequences adopted a well‐defined 9‐helix structure in the solid state and in aprotic and protic organic solvents as well as in aqueous solution.