Octopinic acid

Parthenocissus tricuspidata Planchon. Di Jin (Boston ivy) (root, stem) Cyanidin, lysopine, octopinic acid, fatty acids.48 Treat arthrritis, stomachic, headache, blood in the stool. 

A series of ten opines (mannopine, maimopinic acid, cucumopine, octopine, allo-octopine, octopinic acid, nopaline) and opine analogs (normannopine, galactopine. 

Extracts of crown galls from Nicotiana tabacum, Parthenocissus tricuspidata, and Scorzonera hispanica catalyse the formation of lysopine [JV l-carboxy-ethyl)lysine] from lysine, pyruvic acid, and NADH, and of octopinic acid [Af -(l-carboxycthyl)ornithine] from ornithine, pyruvic acid, and NADH. Extracts from normal tissues of the same plants are unable to catalyse the reactions.[ C]Lysine and diamino[ C]pimelic acid are incorporated into lysopine and into pipecolic acid in crown gall tissue, and it appears likely that lysine in crown gall tissue is not catabolized in the normal way, through pipecolic add or a-aminoadipic acid, but rather transferred into lysopine. 

An aqueous alkaline solution of a mixture of (5)-arginine and pyruvic acid was hydrogenated over platinum oxide to yield (+)-isooctopine (12), a diastereomer of natural octopine, with 70% de (equation 5). Detailed syntheses and properties of the diastereomers of octopine have been reported. ... 

Biosynthesis The biosynthesis from L-Arg and 2-oxo-glutaric acid occurs in plant tumors after infection with Agrobacterium tumefaciens, see also octopine. For synthesis, see Lit. °. 

Arg increases spermatogenesis. Various natural products contain the amino acid, e.g. octopine and the phosphagen, arginine phosphate. Arg was first isolated from lupin seedlings in 1886 by Schulze and Steiger. 

Octopine. Alanine reacts with a-bromopropionic acid in alkaline solution to give a-iminodipropionic acid, which has two asymmetric centers and can exist in two active and one meso form. This reaction has been investigated by Abderhalden and Haase (1931) and by Karrer and Appenzeller (1942) the results were as follows ... 

It is clear that the reaction of the bromo acid with the substituted amine, alanine, is associated with an inversion of the carbon atom derived from the bromo acid. This has a bearing on the configuration of octopine, a constituent of muscle of marine invertebrates. The structure of octopine (I) and the L configuration of that asymmetric carbon which is... 

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