Product of alaptide synthesis: determination of the absolute configuration.

Alaptide is the active substance of the veterinary dermatological ointment ALAPTID and a potential drug in human medicine. Electronic circular dichroism spectroscopy (ECD), transparent spectral region optical rotation (OR), and ab initio calculations were employed to determine the absolute configuration of alaptide. No X-ray structural data determining the absolute configuration were available. It was not possible to employ vibrational circular dichroism spectroscopy (VCD), because alaptide was not sufficiently soluble in common solvents used in VCD spectroscopy to generate reliable spectra. Both ECD spectra and OR values of alaptide solution were in good agreement with predicted data and determined unambiguously the absolute configuration of alaptide synthesized from (S)-alanine as being (S). Copyright (c) 2010 Elsevier B.V. All rights reserved.