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} ;
3D model (JSmol)	Interactive image;
3DMet	B05112;
ChEBI	CHEBI:15805 ;
ChemSpider	414 ; 389221 (2S)-2-Amino ; 97253 (2S)-2-{[(1R)-1-Carboxyethyl]amino} ;
KEGG	C04137 ;
MeSH	octopine
PubChem CID	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(CCCNC(N)=N)C(O)=O)C(O)=O;
Properties
Chemical formula	C9H18N4O4
Molar mass	246.267 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).
	verify (what is ?)
	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

Morizawa, Kiyoshi (1927). "The extractive substances in Octopus octopodia". Acta Scholae Medicinalis Universitatis Imperialis in Kioto. 9: 285–298.
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.
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.
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.

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[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.