Bis(amino acid) derivatives of 1,4-diamino-2-butyne that adopt a C2-symmetric turn conformation.
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.
Curran
Timothy P
TP
Department of Chemistry, Trinity College, Hartford, CT 06106-3100, USA. timothy.curran@trincoll.edu
Marques
Kevin A
KA
Silva
Mark V
MV
D000596:Amino Acids / Q000737:chemistry*; D003959:Diamines / Q000737:chemistry*; D008968:Molecular Conformation; D011522:Protons
D000596:Amino Acids; D003959:Diamines; D011522:Protons; C063335:1,4-diamino-2-butyne