Octopine is a

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

of the

amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 a ...

arginine Arginine is the amino acid with the formula (H2N)(HN)CN(H)(CH2)3CH(NH2)CO2H. The molecule features a guanidinium, guanidino group appended to a standard amino acid framework. At physiological pH, the carboxylic acid is deprotonated (−CO2−) a ...

and

alanine Alanine (symbol Ala or A), or α-alanine, is an α-amino acid that is used in the biosynthesis of proteins. It contains an amine group and a carboxylic acid group, both attached to the central carbon atom which also carries a methyl group sid ...

. It was the first member of the class of chemical compounds known as

opines Opines are low molecular weight compounds found in plant crown gall tumors or hairy root tumors produced by pathogenic bacteria of the genus ''Agrobacterium'' and ''Rhizobium''. Opine biosynthesis is catalyzed by specific enzymes encoded by gen ...

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 An octopus (: octopuses or octopodes) is a soft-bodied, eight-limbed mollusc of the order Octopoda (, ). The order consists of some 300 species and is grouped within the class Cephalopoda with squids, cuttlefish, and nautiloids. Like oth ...

, ''

Pecten maximus ''Pecten maximus'', common names the great scallop, king scallop, St James shell or escallop, is a northeast Atlantic species of scallop, an edible saltwater clam, a marine bivalve mollusc in the family Pectinidae. This is the type species of t ...

'' and ''

Sipunculus nudus ''Sipunculus nudus'' is a cosmopolitan species of unsegmented marine worm of the class Sipuncula, also known as peanut worms. Description As in all peanut worms, the body of ''S. nudus'' consists of a sac-like portion called the trunk and an ever ...

'' where it functions as an analog of

lactic acid Lactic acid is an organic acid. It has the molecular formula C3H6O3. It is white in the solid state and it is miscible with water. When in the dissolved state, it forms a colorless solution. Production includes both artificial synthesis as wel ...

. Plants may also produce this compound after

infection An infection is the invasion of tissue (biology), tissues by pathogens, their multiplication, and the reaction of host (biology), host tissues to the infectious agent and the toxins they produce. An infectious disease, also known as a transmis ...

by ''

Agrobacterium tumefaciens ''Agrobacterium tumefaciens'' (also known as ''Rhizobium radiobacter'') is the causal agent of crown gall disease (the formation of tumours) in over 140 species of eudicots. It is a rod-shaped, Gram-negative soil bacterium. Symptoms are cause ...

'' and transfer of the octopine synthesis gene from the bacterium to the plant. Octopine is formed by reductive

condensation Condensation is the change of the state of matter from the gas phase into the liquid phase, and is the reverse of vaporization. The word most often refers to the water cycle. It can also be defined as the change in the state of water vapor ...

pyruvic acid Pyruvic acid (CH3COCOOH) is the simplest of the keto acids, alpha-keto acids, with a carboxylic acid and a ketone functional group. Pyruvate, the conjugate acid, conjugate base, CH3COCOO−, is an metabolic intermediate, intermediate in several m ...

and arginine through the action of the

NADH Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism. Found in all living cells, NAD is called a dinucleotide because it consists of two nucleotides joined through their phosphate groups. One nucleotide contains an ade ...

-dependent enzyme octopine dehydrogenase (ODH). The reaction is reversible so that pyruvic acid and arginine can be regenerated. : Synthesis octopine

References

{{reflist Alpha-Amino acids Amino acid derivatives Dicarboxylic acids Guanidines