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Volume 271, Number 45, Issue of November 8, 1996 pp. 28002-28005
©1996 by The American Society for Biochemistry and Molecular Biology, Inc.

COMMUNICATION:
Contryphan Is a D-Tryptophan-containing Conus Peptide

(Received for publication, August 19, 1996, and in revised form, September 18, 1996)

Elsie C. Jimenéz Dagger § , Baldomero M. Olivera § , William R. Gray § and Lourdes J. Cruz Dagger §

From the Dagger  Marine Science Institute, University of the Philippines, Diliman, Quezon City 1101, Philippines and the § Department of Biology, University of Utah, Salt Lake City, Utah 84112

In this report, we document for the first time the occurrence of D-tryptophan in a normally translated polypeptide, contryphan. The peptide, isolated from the venom of the fish-hunting marine snail Conus radiatus, produces the ``stiff-tail'' syndrome in mice. Characterization of the octapeptide gave the following sequence,
<AR><R><C>&cjs0822; —————————————————&cjs0822;</C></R><R><C><UP>Gly-Cys-Hyp-<SC>d</SC>-Trp-Glu-Pro-Trp-Cys-NH</UP><SUB><UP>2</UP></SUB></C></R></AR>
<UP>S<SC>equence</SC> 1</UP>
where Hyp = 4-trans-hydroxyproline.

The presence of D-tryptophan in position 4 of contryphan was confirmed by chemical synthesis. The post-translational epimerization in all other D-amino acid-containing small peptides characterized previously from vertebrates and molluscan systems is in position 2.


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