Description
A purine alkaloid, this base was first isolated from the leaves of Gleditsia
triacanthus L., and subsequently discovered in Chidlowia sanguinea and Holar_x0002_rhena floribunda (G. Don.) Dur. et Schinz. The free alkaloid forms colourless
crystals and yields crystalline salts and derivatives, e.g. the hydrochloride, m.p.
218-9°C; hydrobromide, m.p. 215-6°C; sulphate, two salts are formed with
m.p. 175-6°C and 216-7°C respectively depending upon the amount of acid
used in their preparation; picrate, m.p. 246-7°C (dec.); picrolonate, m.p.
229-231 0 C; methiodide, m.p. 227-9°C and the N-benzyl derivative, m.p.
150°C. Oxidation of the alkaloid with KMn04 gives 7-(2:3-dihydroxy-3-methylbutyl)-6-aminopurine which, on periodate oxidation, furnishes 7-(formylmethyl)-
6-aminopurine and Me2CO. Heating the base with Ba(OHh gives one mole each
of NH3, C02 and 4-N-(r:r-dimethylallyl)-N-amino-imidazole-5-carboxamide.
Biochem/physiol Actions
6-(γ,γ-Dimethylallylamino)purine (2iP) is a bacteria-derived riboside cytokinin used to grow plant tissues such as tobacco and soybean callus. 2iP is a precursor of the cytokinin Zeatin. 2iP is used in Schenk and Hildebrandt medium to support in vitro propagation of microshoot cultures from shoot tips of Genista plants.
References
Belikov, Ban'kowsky, Tsarev.,J. Gen. Chern., USSR, 24,919 (1954)
Janot, Cave, Goutarel., Bull. Soc. Chirn. Fr., 896 (1959)
Monseur, Adriaens.,J. Pharrn. Belg., 279 (1960)
Leonard, Deyrup., J. Arner. Chern. Soc., 84, 2148 (1962)
Leonard, Laursen.,J. Org. Chern., 27, 1778 (1962)
Belikov., Ref. Zh. Khirn., 13Zh608 (1970)
