Linear and Cyclic Hybrids of Alternating Thiophene-Amino Acid Units: Synthesis and Effects of Chirality on Conformation and Molecular Packing

Autor:	Dieter Lentz, Michael Wilsdorf, Thien H. Ngo, Hülya Berndt, Hans-Ulrich Reissig
Rok vydání:	2013
Předmět:	chemistry.chemical_classification Dipeptide Chemistry Isostere Stereochemistry Carboxylic acid Organic Chemistry Molecular Conformation Diastereomer Dipeptides Thiophenes General Chemistry Catalysis Stereocenter chemistry.chemical_compound Cyclization Thiophene Amino Acids Protecting group Chirality (chemistry)
Zdroj:	Chemistry - A European Journal. 19:15155-15165
ISSN:	0947-6539
DOI:	10.1002/chem.201302143
Popis:	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.
Databáze:	OpenAIRE
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