Crystal structure of a tripeptide biphenyl hybrid C50H56N6O10•0.5H2O

A peptide biphenyl hybrid compound {systematic name: dimethyl 2,2'-[((2S,2'S)-2,20-{[( 2S,2'S)-1,10-([1,1'-biphenyl]- 2,2'-dicarbonyl)bis(pyrrolidine1,2-diyl-2-carbonyl)] bis( azanediyl)}bis(3-phenylpropanoyl)) bis( azanediyl)]-[2S,2'S)-dipropionate hemihydrate}, C50H56N6O10 center dot 0.5H(2)O, was prepared by coupling of [1,1'-biphenyl]-2,2'-dicarbonyl dichloride, triethylamine and the tripeptide Pro-Phe-Ala in CH2Cl2 at 273 K under an N-2 atmosphere. In the crystal, the asymmetric unit contains the peptide biphenyl hybrid accompanied by one-half of a water molecule. A C atom of one of the proline rings is disordered between two positions in a 0.746 (11):0.254 (11) ratio. An important structural aspect of peptide compounds is their capacity to self-associate mediated by intermolecular and intramolecular hydrogen bonding. This characteristic can be useful in understanding the interactions between peptides and biomacromolecular targets, as well as to explain peptide properties.