We describe the chemical synthesis of the fungal naphthopyrones YWA1 and fonsecin B, as well as their functionalization with an amine-spacer arm and the conjugation of the resulting molecules to three different functional tags (i.e. biotin, Oregon green, PyMPO). The naphthopyrone-biotin and -PyMPO constructs maintained the ability to bind the Ctype lectin receptor MelLec, whose interaction with immunologically active fungal metabolites (i.e. DHN-melanin and YWA1) is a key step in host recognition and induction of protective immune responses against A. fumigatus. The fluorescent Fonsecin B-PyMPO construct 21 was used to selectively visualize MelLec-expressing cells, thus validating the potential of this strategy for studying the role and functions of MelLec in immunity.
|Journal||Journal of Organic Chemistry|
|Publication status||Accepted/In press - 12 Apr 2021|