Abstract
A cytokinin photoaffinity reagent, 8-azido-N 6-benzyladenine (8N3BA), was synthesized from 8-bromoadenosine via azide replacement, benzylation at N−1, rearrangement to the N-6-benzyl derivative and acid hydrolysis. The compound thus obtained was found to have full cytokinin activity in the moss and tobacco cell-suspension bioassays. Photolysis of 8N3BA was accomplished with long and short-wavelength ultraviolet light and produced compounds which had very little or no biological activity in the two bioassays. In-vivo photolysis of 8N3BA caused loss of the cytokinin activity of this compound in moss protonemata. This result was similar to earlier ones where the biological response of moss protonemata to benzyladenine was reversed following removal of the hormone by a short rinse with water.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Abbreviations
- BA:
-
N 6-benzyladenine
- 8N3BA:
-
8-azido-N 6-benzyladenine
- PMR:
-
proton magnetic resonance
- TLC:
-
thin-layer chromatography
- UV:
-
ultraviolet
References
Boyer, J.H., Cantor, F.C.: Alkyl and aryl azides. Chem. Rev. 56, 1–57 (1954)
Brandes, H., Kende, H.: Studies on cytokinin-controlled bud formation in moss protonemata. Plant Physiol. 43, 827–837 (1968)
Cleland, R.E.: Auxin-induced hydrogen ion excretion: correlation with growth, and control by external pH and water stress. Planta (Berl.) 127, 233–242 (1975)
Dammann, L.G., Leonard, N.E.: Cytokinins: synthesis of 2-, 8-, and 2,8-substituted 6-(3-methyl-2-butenylamino)purines and their relative activities in promoting cell growth. Phytochem. 13, 329–336 (1974)
Guthrow, C.E., Rasmussen, H., Brunswick, D.J., Cooperman, B.S.: Specific photo-affinity labeling of the cAMP receptor in intact ghosts from human erythrocytes. Proc. Natl. Acad. Sci. USA 70, 3344–3346 (1973)
Haley, B.E.: Photo-affinity labeling of cAMP binding sites of human red cell membranes. Biochemistry 14, 3852–3857 (1975)
Haley, B.E., Hoffman, J.F.: Interactions of a photo-affinity ATP analogue with cation stimulated ATPases of human red cell membranes. Proc. Natl. Acad. Sci. USA 71, 3367–3371 (1974)
Hanstein, W., Hatefi, Y.: Characterization and localization of mitochondrial uncoupler binding sites with an uncoupler capable of photo-affinity labeling. J. Biol. Chem. 249, 1356–1362 (1974)
Hixson, S.S., Hixson, S.H.: Photochemical labeling of yeast alcohol dehydrogenase with an azide analogue of NAD+. Photochem. and Photobiol. 18, 135–138 (1973)
Holmes, R.E., Robins, R.K.: Purine nucleosides. VII. Direct bromination of adenosine, deoxyadenosine, guanosine, and related purine nucleosides. J. Amer. Chem. Soc. 86, 1242–1245 (1964)
Holmes, R.E., Robins, R.K.: Purine nucleosides. IX. The synthesis of 9-β-D-ribofuranosyl uric acid and other related 8-substituted purine ribonucleosides. J. Amer. Chem. Soc. 87, 1772–1776 (1965)
Knowles, J.R.: Photogenerated reagents for biological receptor-site labeling. Accounts Chem. Res. 5, 155–160 (1972)
Leonard, N.J., Fujii, T.: The synthesis of compounds possessing kinetin activity. The use of a blocking group at the 9-position of adenine for the synthesis of 1-substituted adenines. Proc. Natl. Acad. Sci. USA 51, 73–75 (1964)
Maassen, J.A., Moller, W.: Identification by photo-affinity labeling of the proteins in Escherichia coli ribosomes involved in elongation factor G-dependent GDP binding. Proc. Natl. Acad. Sci. USA 71, 1277–1280 (1974)
Malkinson, A.M., Krueger, B.K., Rudolph, S.A., Casnellie, J.E., Haley, B.E., Greengard, P.: Widespread occurrence of a specific protein in vertebrate tissues and regulation by cAMP of its endogenous phosphorylation and dephosphorylation. Metabolism 24, 331–341 (1975)
Muneyama, K., Bauer, R.J., Shuman, D.A., Robins, R.K., Simon, L.N.: Chemical synthesis and biological activity of 8-substituted cAMP derivatives. Biochemistry 10, 2390–2395 (1971)
Pomerantz, A.H., Rudolph, S.A., Haley, B.S., Greengard, P.: Photo-affinity labeling of a protein kinase from bovine brain with 8-azido-cAMP. Biochemistry 14, 3858–3862 (1975)
Smith, P.A.S., Hall, J.H., Kan, R.O.: The electronic character of the azido group attached to benzene rings. J. Amer. Chem. Soc. 73, 485–489 (1962)
Sussman, M.R., Kende, H.: In vitro cytokinin binding to a particulate fraction of tobacco cells. Planta (submitted)
Tandeau de Marsac, N., Jouanneau, J.: Varlation de l'exigence en cytokinine de lignées clonales de cellules de Tabac. Physiol. Vég. 10, 369–380 (1972)
Theiler, J.B., Leonard, N.J., Schmitz, R.Y., Skoog, F.: Photoaffinity-labeled cytokinins. Plant Physiol. 58, 803–805 (1976)
Whitaker, B.D., Kende, H.: Bud formation in Funaria hygrometrica: A comparison of the activities of three cytokinins with their ribosides. Planta (Berl.) 121, 93–96 (1974)
Author information
Authors and Affiliations
Additional information
In partial fulfillment of requirements for the Ph.D. degree at Michigan State University
Rights and permissions
About this article
Cite this article
Sussman, M.R., Kende, H. The synthesis and biological properties of 8-azido-N 6-benzyladenine, a potential photoaffinity reagent for cytokinin. Planta 137, 91–96 (1977). https://doi.org/10.1007/BF00387544
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00387544