Does anybody have an idea about the biosynthesis of the bioactive
polyhydroxylated lactone, discodermolide.
It has a six-membered lactone ring that is hydroxylated on position 3 and
methylated on position 2 and 4. Further the ring has a 19-carbon long side
chain attached at position five. This side chain is hydroxylated on position
7 (second carbon from the lactone ring), 11, and 17. The side chain is
unsaturated on position 8, 13, 21 and 23, methylated on position 10, 12, 16, 18
and 20, and has a " O-CO-NH2 " chain on position 19. A picture of the structure
can be found in J. Org. Chem, 1990, 55 p 4912-4915.
This compound has been extracted from the Caribbean sponge discodermia dissoluta
and is thought to be an immunosuppressant.
Suggestions about biosyntheses of polyhydroxylated chains and cyclic lactones
are also very welcome.
Thanks a lot, Ernst ter Haar
