Intramolecular hydrogen bonding of (+)-biotin and biotin derivatives in organic solvents

Abstract

The intramolecular hydrogen bonding of (+)-biotin and biotin derivatives in mixtures of CDCl3 and DMSO-d6 was investigated by 1H NMR spectroscopy. The dynamic changes observed in the chemical shifts for the 1-NH and 3-NH protons with changes in solvent composition and temperature confirmed the presence of an intramolecular hydrogen bond between the valeryl side chain hydrogen bond acceptor and the 3-NH proton in a range of biotin derivatives.