Contryphan

Available protein structures:
Pfam	structures / ECOD
PDB	RCSB PDB; PDBe; PDBj
PDBsum	structure summary
PDB	1dfy , 1dfz , 1dg0 , 1nxn , 1qfb

Contryphan
	NMR structure of Contryphan-Vn. The peptide backbone is depicted by a curved tube while the amino acid side-chains are represented by capped sticks. Carbon atoms are colored grey, nitrogen atoms blue, oxygen atoms red, and sulfur atoms yellow.[1]; .
Identifiers
Symbol	Contryphan_CS
Pfam	PF02950
InterPro	IPR011062
PROSITE	PS60027
SCOP2	2cco / SCOPe / SUPFAM
Available protein structures:
Pfam	structures / ECOD
PDB	RCSB PDB; PDBe; PDBj
PDBsum	structure summary
PDB	1dfy , 1dfz , 1dg0 , 1nxn , 1qfb

The contryphans (conus + tryptophan) are a family of peptides that are active constituents of the potent venom produced by cone snail (genus Conus). The two amino acid cysteine residues in contryphans are linked by a disulfide bond. In addition, contryphans undergo an unusual degree of post-translational modification including epimerization of leucine and tryptophan, tryptophan bromination, amidation of the C-terminus, and proline hydroxylation.[2] In the broader scheme of genetic conotoxin classification, contryphans are members of "Conotoxin Superfamily O2."[3]

Family members

Conus textile, which produces contryphans

Contryphan family members include:

Peptide	Sequence	Species	Reference
Des(Gly1)contryphan-R	COwEPWC-NH2	C. radiatus	[4]
Contryphan-R	GCOwEPWC-NH2	Conus radiatus	[4]
Bromocontyphan-R	GCOwEPXC-NH2	C. radiatus	[5]
Contryphan-Sm	GCOwQPWC-NH2	Conus stercusmuscarum	[6]
Contryphan-P	GCOwDPWC-NH₂	C. purpurascens	[6]
Contryphan-R/Tx	GCOwEPWC-NH2	Conus textile	[6]
Contryphan-Tx	GCOWQPYC-NH2	Conus textile	[6]
Contryphan-Vn	GDCPwKPWC-NH₂	Conus ventricosus	[7]
Leu-contryphan-P	GCVlLPWC-OH	Conus purpurascens	[8]
Leu-contryphan-Tx	CVlYPWC-NH₂	Conus textile	[6]
Glaconryphan-M	NγSγCPWHPWC-NH₂	Conus marmoreus	[2]

where the sequence abbreviations stand for:

O = 4-trans-hydroxyproline,
l = D-leucine, L = L-leucine,
w = D-tryptophan, W = L-tryptophan,
γ = gamma-carboxyglutamic acid,
NH₂ = C-terminal amidation

and the remainder of the letters refer to the standard one letter abbreviations for amino acids.

Mechanism of toxicity

The venom of cone snails cause paralysis of their fish prey. The molecular target has not been determined for all contryphan peptides, however it is known that contryphan-Vn is a Ca²⁺-dependent K⁺ channel modulator,[7] while glacontryphan-M is a L-type calcium channel blocker.[2]

References

PDB: 1NXN; Eliseo T, Cicero DO, Romeo C, Schininà ME, Massilia GR, Polticelli F, Ascenzi P, Paci M (June 2004). "Solution structure of the cyclic peptide contryphan-Vn, a Ca²⁺-dependent K⁺ channel modulator". Biopolymers. 74 (3): 189–98. doi:10.1002/bip.20025. PMID 15150794.
Hansson K, Ma X, Eliasson L, Czerwiec E, Furie B, Furie BC, Rorsman P, Stenflo J (July 2004). "The first gamma-carboxyglutamic acid-containing contryphan. A selective L-type calcium ion channel blocker isolated from the venom of Conus marmoreus". The Journal of Biological Chemistry. 279 (31): 32453–63. doi:10.1074/jbc.M313825200. PMID 15155730.
Robinson SD, Norton RS (December 2014). "Conotoxin gene superfamilies". Marine Drugs. 12 (12): 6058–101. doi:10.3390/md12126058. PMC 4278219. PMID 25522317.
Jimenéz EC, Olivera BM, Gray WR, Cruz LJ (November 1996). "Contryphan is a D-tryptophan-containing Conus peptide". The Journal of Biological Chemistry. 271 (45): 28002–5. doi:10.1074/jbc.271.45.28002. PMID 8910408.
Jimenez EC, Craig AG, Watkins M, Hillyard DR, Gray WR, Gulyas J, Rivier JE, Cruz LJ, Olivera BM (February 1997). "Bromocontryphan: post-translational bromination of tryptophan". Biochemistry. 36 (5): 989–94. doi:10.1021/bi962840p. PMID 9033387.
Jacobsen R, Jimenez EC, Grilley M, Watkins M, Hillyard D, Cruz LJ, Olivera BM (March 1998). "The contryphans, a D-tryptophan-containing family of Conus peptides: interconversion between conformers". The Journal of Peptide Research. 51 (3): 173–9. doi:10.1111/j.1399-3011.1998.tb01213.x. PMID 9531419.
Massilia GR, Schininà ME, Ascenzi P, Polticelli F (November 2001). "Contryphan-Vn: a novel peptide from the venom of the Mediterranean snail Conus ventricosus". Biochemical and Biophysical Research Communications. 288 (4): 908–13. doi:10.1006/bbrc.2001.5833. PMID 11688995.
Jacobsen RB, Jimenez EC, De la Cruz RG, Gray WR, Cruz LJ, Olivera BM (August 1999). "A novel D-leucine-containing Conus peptide: diverse conformational dynamics in the contryphan family". The Journal of Peptide Research. 54 (2): 93–9. doi:10.1034/j.1399-3011.1999.00093.x. PMID 10461743.

External links

Contryphan at the US National Library of Medicine Medical Subject Headings (MeSH)

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[pmid15150794-1] PDB: 1NXN; Eliseo T, Cicero DO, Romeo C, Schininà ME, Massilia GR, Polticelli F, Ascenzi P, Paci M (June 2004). "Solution structure of the cyclic peptide contryphan-Vn, a Ca²⁺-dependent K⁺ channel modulator". Biopolymers. 74 (3): 189–98. doi:10.1002/bip.20025. PMID 15150794.

[pmid15155730-2] Hansson K, Ma X, Eliasson L, Czerwiec E, Furie B, Furie BC, Rorsman P, Stenflo J (July 2004). "The first gamma-carboxyglutamic acid-containing contryphan. A selective L-type calcium ion channel blocker isolated from the venom of Conus marmoreus". The Journal of Biological Chemistry. 279 (31): 32453–63. doi:10.1074/jbc.M313825200. PMID 15155730.

[3] Robinson SD, Norton RS (December 2014). "Conotoxin gene superfamilies". Marine Drugs. 12 (12): 6058–101. doi:10.3390/md12126058. PMC 4278219. PMID 25522317.

[pmid8910408-4] Jimenéz EC, Olivera BM, Gray WR, Cruz LJ (November 1996). "Contryphan is a D-tryptophan-containing Conus peptide". The Journal of Biological Chemistry. 271 (45): 28002–5. doi:10.1074/jbc.271.45.28002. PMID 8910408.

[pmid9033387-5] Jimenez EC, Craig AG, Watkins M, Hillyard DR, Gray WR, Gulyas J, Rivier JE, Cruz LJ, Olivera BM (February 1997). "Bromocontryphan: post-translational bromination of tryptophan". Biochemistry. 36 (5): 989–94. doi:10.1021/bi962840p. PMID 9033387.

[pmid9531419-6] Jacobsen R, Jimenez EC, Grilley M, Watkins M, Hillyard D, Cruz LJ, Olivera BM (March 1998). "The contryphans, a D-tryptophan-containing family of Conus peptides: interconversion between conformers". The Journal of Peptide Research. 51 (3): 173–9. doi:10.1111/j.1399-3011.1998.tb01213.x. PMID 9531419.

[pmid11688995-7] Massilia GR, Schininà ME, Ascenzi P, Polticelli F (November 2001). "Contryphan-Vn: a novel peptide from the venom of the Mediterranean snail Conus ventricosus". Biochemical and Biophysical Research Communications. 288 (4): 908–13. doi:10.1006/bbrc.2001.5833. PMID 11688995.

[pmid10461743-8] Jacobsen RB, Jimenez EC, De la Cruz RG, Gray WR, Cruz LJ, Olivera BM (August 1999). "A novel D-leucine-containing Conus peptide: diverse conformational dynamics in the contryphan family". The Journal of Peptide Research. 54 (2): 93–9. doi:10.1034/j.1399-3011.1999.00093.x. PMID 10461743.