MODIFIED ASCARASIDES

Claims

This application relates to ascarosides with side chains derived from modified fatty acids. The application also relates to methods of using these modified ascarosides.

1. A compound of formula (1) or a salt thereof; wherein: each of R a and R b is independently -H, or an optionally substituted moiety selected from the group consisting of: a C1-20 aliphatic group, a C1-20 acyl group, a C1-20 heteroaliphatic group, aryl, heteroaryl, a hydroxyl protecting group, a phosphorus-bonded functional group, a sulfur-bonded functional group, a silicon-bonded functional group, a C2-20 carbonate (e.g., a -C(O)OR c moiety), a C2-20 carbamate (e.g., a -C(O)N(R c)2 moiety), a C2-20 thioester (e.g., a -C(S)R c moiety), a C2-20 thiocarbonate (e.g., a -C(S)OR c moiety), a C2-20 dithiocarbonate (e.g., a -C(S)SR c moiety), a C1-20 thiocarbamate (e.g., a -C(S)N(R c )2 residue), a sugar residue, a peptide, a polymer chain or a connection through a link or carbon-containing linking residue to another ascaroside molecule;each Rc is independently selected at each occurrence of -H, an optionally substituted C1-12 aliphatic group, an optionally substituted C1-12 heteroaliphatic group, an optionally substituted aryl group, an optionally substituted heteroaryl group, a polymer chain, or a linkage or linking residue containing carbon to another ascaroside molecule, and wherein R a and R b can be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation; and -Z comprises an optionally unsaturated, optionally substituted C2-40 side chain terminating in a chain end comprising a functional group containing nitrogen, oxygen, or sulfur and having at least one non-hydrogen substituent on carbon atoms that are adjacent to or two atoms away from the chain end.