Facile synthesis of tilmicosin and tylosin related haptens for use as protein conjugates

Synthesis is described for the haptens 23-demycinosyl-23-deoxy-23-(3-aminoprop-1-yl)-aminotilmicosin (6) from 5-O-mycaminosyltylonolide (OMT) and for 23-demycinosyl-23-deoxy-23-(3-aminoprop-1-yl)-amino-20-dihydrotylosin (10) from demycinosyltylosin (DMT), respectively. The mild reaction conditions used to synthesize the second hapten, DMT derivative 10, were necessary to overcome instabilities and acid lability of DMT. The haptens synthesized here may be further used to produce protein conjugates useful in developing antibodies against the antibiotics tilmicosin and tylosin.