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Synthesis and structural characterization of amino acid and peptide derivatives featuringN-(p-bromobenzoyl) substituents as promising connection unit for bio-inspired hybrid compounds

Authors
Journal
Journal of Molecular Structure
0022-2860
Publisher
Elsevier
Publication Date
Volume
994
Identifiers
DOI: 10.1016/j.molstruc.2011.03.058
Keywords
  • N-(P-Bromobenzoyl) Amino Acid
  • N-(P-Bromobenzoyl) Peptide
  • X-Ray Crystal Structure
  • Hydrogen Bonding
  • Strand Packing Motif
  • Peptide Sheet Structure

Abstract

Abstract Using a sequence of activation, blocking and peptide coupling procedures, a series of ten amino acid and peptide derivatives 1– 6 ( a, b, respectively) featuring a p-bromobenzoyl substituent attached to the amino group of the parent compound has been synthesized. X-ray crystal structures of two corresponding amino acid ( 1a, 1b), two amino acid ester ( 3a, 3b) and three peptide ester derivatives ( 4a, 4b, 5b) are reported, with the amide and peptide bonds of the molecules all being planar and trans configurated. Intramolecular interactions dominating the packing motifs and thus giving rise to the formation of strands ( 1a, 3a, 3b, 4a, 4b), molecular pairs ( 1b) or sheets ( 5b) derive from N–H⋯O contacts, being further assisted by O–H⋯O and weaker C–H⋯O interactions, while bromo involved contacts are of minor importance.

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