Teicoplanin, antibiotics from Actinoplanes teichomyceticus nov. sp. VI. Chemical degradation: physico-chemical and biological properties of acid hydrolysis products

Abstract

Teicoplanin is an antibiotic complex consisting of five closely related factors, T-A2-1, 2, 3, 4 and 5 and a more polar factor, T-A3-1. By controlled acid hydrolysis the complex is transformed into pseudoaglycones and finally into a single aglycone with consecutive removal of three sugar units. Quantitative determination of sugars obtained by degradative reactions and NMR/LC-MS studies on suitable derivatives confirmed that all the components carry one N-acyl-D-glucosamine and that at least two of them are characterized by N-decanoyl and N-undecanoyl chains on the D-glucosamine unit. The hydrolysis products still possess in vitro and in vivo activity.