CYTOKININS: SYNTHESIS OF 6-(3-METHYL-3-BUTENYLAMINO)-9-beta-D-RIBOFURANOSYLPURINE (3IPA), AND THE EFFECT OF SIDE-CHAIN UNSATURATION ON THE BIOLOGICAL ACTIVITY OF ISOPENTYLAMINOPURINES AND THEIR RIBOSIDES.

doi:10.1073/PNAS.59.1.15

Paper

CYTOKININS: SYNTHESIS OF 6-(3-METHYL-3-BUTENYLAMINO)-9-beta-D-RIBOFURANOSYLPURINE (3IPA), AND THE EFFECT OF SIDE-CHAIN UNSATURATION ON THE BIOLOGICAL ACTIVITY OF ISOPENTYLAMINOPURINES AND THEIR RIBOSIDES.

Published 1968 · N. J. Leonard, S. M. Hecht, F. Skoog

Proceedings of the National Academy of Sciences of the United States of America

Q1 SJR score

34

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

6-(y,7y-Dimethylallylamino)purine (VII), 2iP, which was initially obtained synthetically,1' 2 has been shown to be a highly active,3-7 naturally occurring cytokinin., 9 The corresponding ribosyl derivative, 6-(y, y-dimethylallylamino)-9-3-D-ribofuranosylpurine (VIII), 2iPA, is also biologically activel0-12 and has been shown to occur naturally in serine and tyrosine tRNA's.11-20 These findings suggested that 6-(3-methyl-3-butenylamino)purine (V),21 3iP, and 6-(3-methyl-3-butenylamino)-9-f-D-ribofuranosylpurine (VI), 3iPA, might also possess cytokinin activity because of the biological equivalence of the A2and A3-isopentenyl groups, at least at the pyrophosphate stage in biosynthesis.22-25 In amplification of the outline provided for the synthesis of 3iP (V),21 3methyl-3-buten-l-yl p-toluenesulfonate was prepared by treating the corresponding alcohol with p-toluenesulfonyl chloride in pyridine at 0? for 24 hours, followed by destruction of the excess acid chloride with water, extraction of the products from the aqueous phase with ether, and treatment of the ether extracts sequentially with acid, base, water, and drying agent. Concentration of the ether solution afforded a liquid (92% yield), characterized by microanalysis (calculated for C12H16SO3: C, 59.97; H, 6.71; found: C, 60.03; H, 7.09)

Study Snapshot

This study successfully synthesized 6-(3-methyl-3-butenylamino)-9-beta-D-ribofuranosylpurine (3IPA) and its ribosyl derivative, demonstrating its biological activity as a potential cytokinin.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

CYTOKININS: SYNTHESIS OF 6-(3-METHYL-3-BUTENYLAMINO)-9-beta-D-RIBOFURANOSYLPURINE (3IPA), AND THE EFFECT OF SIDE-CHAIN UNSATURATION ON THE BIOLOGICAL ACTIVITY OF ISOPENTYLAMINOPURINES AND THEIR RIBOSIDES.

Sign up to use Study Snapshot

References

Citations

N⁶-Alkyladenosines: Synthesis and evaluation of in vitro anticancer activity.

N6-alkyladenosines show anti-proliferative activity against bladder cancer cells, but have no effect on cell invasion or metalloprotease activity.

Novel Isopentenyladenosine Analogues: Synthesis, Characterization, and Evaluation of Antiproliferative Activity on Bladder Carcinoma Cells

Isopentenyladenosine (iPA) inhibits bladder cancer cell proliferation but not migration, and its cytostatic activity requires the integrity of the ribose ring.

Regulation of source/sink relations by cytokinins

Cytokines play a crucial role in regulating source-sink relations in plants, with their molecular prerequisite being the induction of extracellular invertase and hexose transporters.

Regulation and function of extracellular invertase from higher plants in relation to assimilate partitioning, stress responses and sugar signalling

Extracellular invertase plays a crucial role in plant development, regulating assimilate partitioning, defense reactions, and sugar signal transduction pathways.

Benzyladenine and derivatives-their significance and interconversion in plants

Benzyladenine, a natural cytokinin found in various plants, alters the understanding of this hormone's role and metabolism, with its biosynthesis still unknown.