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Linear and Cyclic Hybrids of Alternating Thiophene–Amino Acid Units: Synthesis and Effects of Chirality on Conformation and Molecular Packing
Author(s) -
Ngo Thien H.,
Berndt Hülya,
Wilsdorf Michael,
Lentz Dieter,
Reissig HansUlrich
Publication year - 2013
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.201302143
Subject(s) - stereocenter , isostere , dipeptide , diastereomer , chemistry , ring (chemistry) , chirality (physics) , stereochemistry , combinatorial chemistry , amino acid , enantioselective synthesis , organic chemistry , catalysis , chiral symmetry , biochemistry , nambu–jona lasinio model , physics , quantum mechanics , quark
The dipeptide isostere 5‐aminothiophene carboxylic acid has been combined with L ‐phenylalanine moieties to provide linear and cyclic hybrid oligopeptides. A suitable protecting group strategy and appropriate coupling methods have been developed to guarantee a high degree of enantiopurity of the resulting amides. Cyclic tetraamides have been efficiently obtained by macrocyclization of the linear derivatives. In the case of racemized cyclization precursors, two diastereomeric macrocycles ( S , S / R , R and meso ) have been isolated. Their crystal structures show clear effects of the stereogenic centers on the ring conformations and molecular packing.