From owner-metabolic-reg@net.bio.net Thu Nov 09 22:00:00 1995
Path: biosci!bcm.tmc.edu!news.msfc.nasa.gov!newsfeed.internetmci.com!in1.uu.net!newsfeed.pitt.edu!vms.cis.pitt.edu!ethst
From: ethst@vms.cis.pitt.edu
Newsgroups: bionet.metabolic-reg
Subject: discodermolide biosynthesis?
Date: 10 Nov 95 17:21:04 EDT
Organization: University of Pittsburgh
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Message-ID: <480j9m$d23@usenet.srv.cis.pitt.edu>
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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


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