title: Bis(amino acid) derivatives of 1,4-diamino-2-butyne that adopt a C2-symmetric turn conformation.
abstract: 1,4-Diamino-2-butyne was prepared from 1,4-dichloro-2-butyne via 1,4-diazido-2-butyne. Bis(amino acid) derivatives of 1,4-diamino-2-butyne having the general structure (Boc-Xxx-NHCH2C[triple bond])2 (Xxx = Ala, Phe and Met) were prepared and examined by 1H NMR spectroscopy. Using chemical shift, coupling constant and DMSO titration data it is found that these compounds adopt a C2-symmetric turn conformation featuring two intramolecular hydrogen bonds.
authors.affiliation: Department of Chemistry, Trinity College, Hartford, CT 06106-3100, USA. timothy.curran@trincoll.edu
authors.forename: Timothy P
authors.initials: TP
authors.lastname: Curran
authors.forename: Kevin A
authors.initials: KA
authors.lastname: Marques
authors.forename: Mark V
authors.initials: MV
authors.lastname: Silva
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D003959:Diamines / Q000737:chemistry*; D008968:Molecular Conformation; D011522:Protons
chemical_list: D000596:Amino Acids; D003959:Diamines; D011522:Protons; C063335:1,4-diamino-2-butyne