@article{39682c4d071d4bbb9764d12ee8fd4665,
title = "Cytokinins: Synthesis and growth-promoting activity of 2-substituted compounds in the N6-isopentenyladenine and zeatin series",
abstract = "Fourteen compounds were tested for relative promotion of cell division and growth (cytokinin) activity in the tobacco bioassay. The results suggested that 2-substituted-N6-(hydroxy)isopentenylaminopurines were generally less active than their unsubstituted couterparts. Thus, a 2-OH substituent greatly lowered cytokinin activity in both the isopentenyl and hydroxyisopentenyl (zeatin) series, while 2-NH2 and 2-SCH3 groups had a lesser effect on activity and a 2-Cl substituent had a negligible effect. Mass spectra were determined for all of the 9-β-d-ribofuranosides and for a number of the purines as well; the fragmentation patterns were consistent and characteristic, providing a possible systematic approach to the identification of new 2-substituted-N6-(hydroxy)isopentenyladenines.",
author = "Hecht, {Sidney M.} and Leonard, {Nelson J.} and Schmitz, {Ruth Y.} and Folke Skoog",
note = "Funding Information: INTRODUCTION Two NUCLEOGIDErSes ponsible for cytokinin activity in Escherichiu coli tRNA{\textquoteright}s have been isolated and identified in these laboratories as 6(3-methyl-2-butenylamino)-2-methylthio FD-ribof-uranosylpurine [V-(d2-isopentenyl)-2-methylthioadenosine] (ms2iPA) (IIc){\textquoteleft}~ 2 and 6-(3-methyI-2-butenylamino)-9-B_D-ribof~anosylp~ne[~6-(~2-iso~~nyl)ad~o~neJ (2iPA) (II, R = H).z To facilitate the identification of other 2-substituted adenine derivatives possibly occurring in tRNA and to establish relationships between natural occurrence, substitution, and cytokinin activity, we have synthesized and tested a series of W-(3-methyl-2-butenyl)adenines (Ia-d) and adenosines (1Ia-c). In addition, we have examined a similar series of 2-substituted compounds related to zeatin, 6-(4hydroxy-3-methyl-trans-2-butenylamino)purine (I, R = H, R{\textquoteright} = 0H).3-g The compounds selected had 2-hydroxy * Supported at the Univezsity of Illinois by a research grant (GM-05829) from the National Institutes of Health, U.S. Public Health &vice, and at the University of Wisamsin by a resear& grant (GB-6994X) from the National Science Foundation and by the Research Committee of the Graduate School with funds from the Wisconsin Alumni Research Foundation. t National Institutea of Health Predoctoral Fellow, 1967-70. Present address: Laboratory of Molecular Biology, University of Wisconsin, Madison, Wisconsin, U.S.A. 1 W. J. BURROWSD, . J. mm, F. S. M. HKHT, J. T. A. BOYLE,N. J. bONARD and J. Occom, Science 161,691(1968).",
year = "1970",
month = jun,
doi = "10.1016/S0031-9422(00)85305-4",
language = "English (US)",
volume = "9",
pages = "1173--1180",
journal = "Phytochemistry",
issn = "0031-9422",
publisher = "Elsevier Limited",
number = "6",
}