Octopine

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Not to be confused with octopamine.
Octopine
Stereo, skeletal formula of octopine ((2S)-2-{[(1R)-1-carboxyethyl]amino})
Identifiers
CAS number 34522-32-2 (2S)-2-{[(1R)-1-Carboxyethyl]amino} N
PubChem 427, 440237 (2S)-2-Amino, 12313676 (2S)-2-{[(1S)-1-Carboxyethyl]amino}, 108172 (2S)-2-{[(1R)-1-Carboxyethyl]amino}
ChemSpider 414 N, 389221 (2S)-2-Amino YesY, 97253 (2S)-2-{[(1R)-1-Carboxyethyl]amino} YesY
KEGG C04137 N
MeSH octopine
ChEBI CHEBI:15805 YesY
3DMet B04929
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C9H18N4O4
Molar mass 246.26 g mol−1
Related compounds
Related alkanoic acids
Related compounds
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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.

Synthesis octopine.svg

References[edit]

  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.