Conformational switching caused by biphenyl substitution at the Calpha position: ethyl 2-benzyl-2-(formylamino)-3-phenylpropionate and ethyl 3-(1,1'-biphenyl-4-yl)-2-(formylamino)-2-(4-phenylbenzyl)propionate.
The title compounds, C19H21NO3 and C31H29NO3, are derivatives of alpha-aminoisobutyric acid, with benzyl and dibenzyl substitution. The pseudo-peptide formed by the N-formyl and ethyl ester substitution at the Calpha position switches from a trans-trans to a trans-cis configuration as a result of biphenyl substitution. The packing of the compounds is stabilized by N-H...O and C-H...O hydrogen bonds.
Damodharan
Lakshminarasimhan
L
Department of Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India.
Pattabhi
Vasantha
V
Behera
Manoranjan
M
Kotha
Sambasivarao
S
D000621:Aminoisobutyric Acids / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D001713:Biphenyl Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008968:Molecular Conformation
D000621:Aminoisobutyric Acids; D001593:Benzyl Compounds; D001713:Biphenyl Compounds; C100049:2-aminoisobutyric acid