N¹⁵-ALKYL AND N¹⁵, N¹⁵-DIALKYL DERIVATIVES OF TEICOPLANIN ANTIBIOTICS

Abstract

The synthesis and the biological properties of a series of N¹⁵-alkyl and N¹⁵, N¹⁵-dialkyl derivatives of teicoplanin A2, its pseudoaglycones and aglycone are described.
The alkylation of the terminal amino group did not affect the ability of these teicoplanin derivatives to bind with Ac₂-L-Lys-D-Ala-D-Ala, a synthetic model of the antibiotic's target peptide in bacterial cell walls, but influenced their in vitro and in vivo antimicrobial activities to a different extent, depending on the structure and length of the alkyl chains and the type and number of sugars present.