N6-(delta 2-Isopentenyl)-adenine

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.

The Uses of N6-(delta 2-Isopentenyl)-adenine

N6-(2-Isopentenyl)adenine can be used in biological study for cytokinins stimulated expression of stress-related proteins and transcripts in Arabidopsis thaliana with isopentenyltransferase overexpression.

The Uses of N6-(delta 2-Isopentenyl)-adenine

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 has been used in Schenk and Hildebrandt medium to support in vitro propagation of microshoot cultures from shoot tips of Genista plants.

What are the applications of Application

N-6-(Δ2-Isopentenyl)-adenine is a weakly active olomoucine

Definition

ChEBI: A 6-isopentenylaminopurine in which has the isopentenyl double bond is located between the 2 and 3 positions of the isopentenyl group.

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)