Octopine

Octopine
Stereo, skeletal formula of octopine ((2S)-2-{[(1R)-1-carboxyethyl]amino})
Stereo, skeletal formula of octopine ((2S)-2-{[(1R)-1-carboxyethyl]amino})
Names
IUPAC name
2-[[1-Carboxyethyl]amino]-5-(diaminomethylideneamino)pentanoic acid[citation needed]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
MeSH octopine
  • 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)/t5-,6+/m1/s1 checkY
    Key: IMXSCCDUAFEIOE-RITPCOANSA-N checkY
  • C[C@@H](N[C@@H](CCCNC(N)=N)C(O)=O)C(O)=O
Properties
C9H18N4O4
Molar mass 246.267 g·mol−1
Related compounds
Related alkanoic acids
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

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. Plants may also produce this compound after infection by Agrobacterium tumefaciens and transfer of the octopine synthesis gene from the bacterium to the plant.

Biosynthesis

Octopine is formed by reductive condensation of the amino acid, L-arginine, with pyruvic acid through the action of the nicotinamide adenine dinucleotide-dependent enzyme octopine dehydrogenase. The reaction is reversible so that pyruvic acid and arginine can be regenerated. This has the important effect of regulating the amount of the cofactor available as NAD+.

2D representation of the chemical structure of arginine.
arginine
+ NADH +
 
2D representation of the chemical structure of pyruvic acid .
pyruvic acid
 
H+
H2O
Reversible left-right reaction arrow with minor forward substrate(s) from top left, minor forward product(s) to top right, minor reverse substrate(s) from bottom right and minor reverse product(s) to bottom left
H+
H2O
 
2D representation of the chemical structure of Q2013941.
D-octopine
+ NAD+
 

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. Bibcode:1977Sci...195...72H. doi:10.1126/science.831256. PMID 831256.
  3. ↑ Hooykaas, Paul J. J.; Schilperoort, Rob A. (1 May 1992). "Agrobacterium and plant genetic engineering". Plant Molecular Biology. 19 (1): 15–38. doi:10.1007/BF00015604. PMID 1600167. S2CID 36172990.
  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.
  5. ↑ van Os N, Smits SH, Schmitt L, Grieshaber MK (2012). "Control of D-octopine formation in scallop adductor muscle as revealed through thermodynamic studies of octopine dehydrogenase". Journal of Experimental Biology. 215 (9): 1515–1522. Bibcode:2012JExpB.215.1515V. doi:10.1242/jeb.069344. PMID 22496288.
  6. ↑ Strahl J, Dringen R, Schmidt MM, Hardenberg S, Abele D (2011). "Metabolic and physiological responses in tissues of the long-lived bivalve Arctica islandica to oxygen deficiency". Comparative Biochemistry and Physiology A. 158 (4): 513–519. doi:10.1016/j.cbpa.2010.12.015. PMID 21184842.