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Structural studies on monofluorinated derivatives of the phytohormone indole-3-acetic acid (auxin) (CROSBI ID 77584)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Antolić, Snježana ; Kojić-Prodić, Biserka ; Tomić, Sanja ; Nigović, Biljana ; Magnus, Volker ; Cohen, Jerry D. Structural studies on monofluorinated derivatives of the phytohormone indole-3-acetic acid (auxin) // Acta crystallographica. Section B, Structural science, 52 (1996), 4; 651-661. doi: 10.1107/S0108768195016302

Podaci o odgovornosti

Antolić, Snježana ; Kojić-Prodić, Biserka ; Tomić, Sanja ; Nigović, Biljana ; Magnus, Volker ; Cohen, Jerry D.

engleski

Structural studies on monofluorinated derivatives of the phytohormone indole-3-acetic acid (auxin)

As a part of molecular recognition studies on the phytohormone indole-3-acetic acid (IAA), a series of fluorinated IAAs was examined. Substitution at positions 4, 5, 6 and 7 of the phenyl ring resulted in four compounds, which were analyzed. Structure-activity considerations included the analysis of molecular conformation, based on the results of X-ray diffraction studies and computational chemistry, of lipophilicity and of UV absorbance, as well as bioactivity determinations in the Avena coleoptile and the Pisum sativum stem straight-growth tests. The conformations of monofluorinated IAAs and the unsubstituted parent compound are defined by rotation about two bonds: one determines the relative orientation of the side chain towards the indole plane and the second the orientation of the carboxylic group. The results of X-ray structure analysis revealed the folded shape of the molecules in all compounds studied. Molecular mechanics and dynamics located the folded shape as the local minimum, but failed to detect the planar conformation as one of the minima, which according to ab initio results on IAA and 4-Cl-IAA could also be possible.

X-ray structure analysis ; lipophilicity ; bioassays ; auxins ; indole-3-acetic acid ; monofluorinated indole-3-acetic acids

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Podaci o izdanju

52 (4)

1996.

651-661

objavljeno

0108-7681

1600-5740

10.1107/S0108768195016302

Povezanost rada

Kemija

Poveznice
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