title: N-acetyl-N'-methylamide derivative of (2S,3S)-1-amino-2,3-diphenylcyclopropanecarboxylic acid: theoretical analysis of the conformational impact produced by the incorporation of the second phenyl group to the cyclopropane analogue of phenylalanine.
abstract: The intrinsic conformational preferences of (2S,3S)-1-amino-2,3-diphenylcyclopropanecarboxylic acid, a phenylalanine cyclopropane analogue bearing two phenyl substituents, have been examined theoretically. For this purpose, its N-acetyl-N'-methylamide derivative, Ac-(2S,3S)c(3)diPhe-NHMe, has been investigated by using ab initio HF and DFT methods. Results have been compared with those previously reported for other cyclopropane analogues of phenylalanine, and with experimental data available for c(3)diPhe-containing peptides.
authors.affiliation: Departament de Química, Escola Universitària Politècnica, Universitat de Lleida, c/Jaume II No. 69, 25001 Lleida, Spain. jcasanovas@quimica.udl.es
authors.forename: Jordi
authors.initials: J
authors.lastname: Casanovas
authors.forename: Ana I
authors.initials: AI
authors.lastname: Jiménez
authors.forename: Carlos
authors.initials: C
authors.lastname: Cativiela
authors.forename: Juan J
authors.initials: JJ
authors.lastname: Pérez
authors.forename: Carlos
authors.initials: C
authors.lastname: Alemán
mesh_terms: D003521:Cyclopropanes / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008744:Methylamines / Q000138:chemical synthesis*; D008958:Models, Molecular; D008968:Molecular Conformation; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D012996:Solutions; D012997:Solvents; D013816:Thermodynamics
chemical_list: C481928:(2S,3S)-1-amino-2,3-diphenylcyclopropanecarboxylic acid; D003521:Cyclopropanes; D007202:Indicators and Reagents; D008744:Methylamines; D012996:Solutions; D012997:Solvents; D010649:Phenylalanine