Octopine

Octopine

Names
IUPAC name 2-[[1-Carboxyethyl]amino]-5-(diaminomethylideneamino)pentanoic acid
Identifiers
CAS Number	34522-32-2 (2S)-2-{[(1R)-1-Carboxyethyl]amino}
3DMet	B04929
ChEBI	CHEBI:15805
ChemSpider	414 389221 (2S)-2-Amino 97253 (2S)-2-{[(1R)-1-Carboxyethyl]amino}
Jmol interactive 3D	Image Image
KEGG	C04137
MeSH	octopine
PubChem	427 440237 (2S)-2-Amino 12313676 (2S)-2-{[(1S)-1-Carboxyethyl]amino} 108172 (2S)-2-{[(1R)-1-Carboxyethyl]amino}
InChI InChI=1S/C9H18N4O4/c1-5(7(14)15)13-6(8(16)17)3-2-4-12-9(10)11/h5-6,13H,2-4H2,1H3,(H,14,15)(H,16,17)(H4,10,11,12) Key: IMXSCCDUAFEIOE-UHFFFAOYSA-N
SMILES CC(NC(CCC[nH]:c(:[nH]):[nH2])c(:[o]):[oH])c(:[o]):[oH] CC(NC(CCCNC(N)=N)C(O)=O)C(O)=O
Properties
Chemical formula	C9H18N4O4
Molar mass	246.27 g·mol^−1
Related compounds
Related alkanoic acids	Daminozide Nopaline
Related compounds	Bis-tris propane Pantetheine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Octopine is a derivative of the amino acids arginine and alanine. It was the first member of the class of chemical compounds known as opines to be discovered. Octopine gets its name from Octopus octopodia from which it was first isolated in 1927.^[1]

Octopine has been isolated from the muscle tissue of invertebrates such as octopus, Pecten maximus and Sipunculus nudus where it functions as an analog of lactic acid.^[2] It is also produced by Agrobacterium and causes crown gall tumor growth in plants.^[3]

Octopine is formed by reductive condensation of pyruvic acid and arginine through the action of the NADH-dependent enzyme octopine dehydrogenase (ODH).^[4] The reaction is reversible so that pyruvic acid and arginine can be regenerated.

References

1. Morizawa, Kiyoshi (1927). "The extractive substances in Octopus octopodia". Acta Scholae Medicinalis Universitatis Imperialis in Kioto 9: 285–298.
2. Hockachka, P.; Hartline, P.; Fields, J. (1977). "Octopine as an end product of anaerobic glycolysis in the chambered nautilus". Science 195 (4273): 72–4. doi:10.1126/science.831256. PMID 831256.
3. Lippincott, James A.; Lippincott, Barbara B. (1970). "Lysopine and octopine promote crown-gall tumor growth in vivo". Science 170 (3954): 176–177. doi:10.1126/science.170.3954.176. PMID 17833501.
4. Smits, Sander H.J.; Mueller, Andre; Schmitt, Lutz; Grieshaber, Manfred K. (2008). "A Structural Basis for Substrate Selectivity and Stereoselectivity in Octopine Dehydrogenase from Pecten maximus". Journal of Molecular Biology 381 (1): 200–11. doi:10.1016/j.jmb.2008.06.003. PMID 18599075.