Glycopeptide antibiotics (especially vancomycin) are a clinically important family of antibiotics reserved for treating multidrug resistant bacteria1. The high complexity of the tricyclic molecule has made its development slow and hampered the success of these otherwise powerful compounds2. The use of enzymes in organic synthesis can be a powerful tool to help access complex molecules like vancomycin and aid in the development of new analogues3. Herein a bio-inspired approach of solid-phase peptide synthesis followed by the introduction of three side chain-side chain crosslinks using an enzymatic cascade is presented. This work shows that novel glycopeptide antibiotic analogues can be accessed rapidly via enzymatic catalysis.