Octopine

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