Contryphan is a D-tryptophan-containing Conus peptide.
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, Gly-Cys-Hyp-D-Trp-Glu-Pro-Trp-Cys-NH2 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.
Marine Science Institute, University of the Philippines, Diliman, Quezon City 1101, Philippines.
E C
EC
Jimenéz
B M
BM
Olivera
W R
WR
Gray
L J
LJ
Cruz
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D051379:Mice; D008978:Mollusk Venoms / Q000737:chemistry*; D009043:Motor Activity / Q000187:drug effects; D010455:Peptides / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000008:administration & dosage / Q000737:chemistry* / Q000494:pharmacology; D012908:Snails; D014364:Tryptophan
D008978:Mollusk Venoms; D010455:Peptides; D010456:Peptides, Cyclic; C102355:contryphan; D014364:Tryptophan