Expeditious synthesis and chromatographic resolution of (+)- and (?)-trans-1-benzylcyclohexan-1,2-diamine hydrochlorides

Abstract

The hitherto unknown (-)- and (+)-1-benzylcyclohexan-1,2-diamine hydrochlorides 4a. HCl and 4b. HCl were synthesized by means of diastereoselective alpha-iminoamine rearrangement with subsequent imine reduction and hydrogenolysis. The relative trans-configuration as well as the absolute (1S,2R) and (1R,2S) configurations of 4a and 4b, respectively, were elucidated on the basis of an X-ray analysis of 3b. HCl. The enantiomeric excess (ee) values of the title compounds (>99%) were determined by chiral HPLC on a Chirex (D) Penicillamine column.

Anti-inflammatory effects of peptides from a marine algicolous fungus Acremonium sp. NTU492 in BV-2 microglial cells

“…The chirality of each amino acid of 1 – 4 was analyzed by HPLC as described previously in the literature [ 6 ]. Compounds 1 – 4 (each 1.5 mg) were subjected to hydrolysis with 6N HCl (0.5 mL) in a sealed tube at 110 °C for 20 h. Upon cooling, the acid in the hydrolysate was removed by Sep-Pak C 18 SPE column (0.5 g, Waters), and the analyte eluted by aqueous methanol was subjected to chiral analysis on a Chirex 3126 ( d )-penicillamine column, 4.6 i.d.…”