Evaluation of the macrocyclic glycopeptide A-40,926 as a high-performance liquid chromatographic chiral selector and comparison with teicoplanin chiral stationary phase

A new macrocyclic antibiotic of the vancomycin family, referred to by its i ndustrial designation as A-40,926, was bonded to 5 mum silica particles and utilised as a chiral stationary phase (CSP). Since A-40,926 is structurall y related to teicoplanin, the A-40,926 CSP was compared to a commercially a vailable teicoplanin CSP. A set of 28 chiral compounds, including amino-aci ds and related compounds, compounds with a ring containing the stereogenic centre, compounds bearing aromatic structures near their stereogenic centre s and alcohols, was tested for enantioseparation on the two CSPs. The resul ts are compared and discussed in terms of enantioselective Gibbs energy dif ference. The A-40,926 CSP was able to resolve one compound that was not res olved by the teicoplanin CSP. However, it could not separate four compounds that the teicoplanin CSP did separate. It is shown that the A-40,926 CSP i s complementary to the teicoplanin CSP, thereby enlarging the number of ena ntiomers that can be separated by the macrocyclic glycopeptide based CSPs. (C) 2000 Elsevier Science B.V. All rights reserved.