Structural characterization and auxin properties of dichlorinated indole-3-acetic acids

Snježana Antolić; Branka Salopek; Biserka Kojić-Prodić; Volker Magnus; Jerry D. Cohen

doi:10.1023/A:1006031527789

Structural characterization and auxin properties of dichlorinated indole-3-acetic acids

Snježana Antolić, Branka Salopek, Biserka Kojić-Prodić, Volker Magnus, Jerry D. Cohen

Horticultural Science

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

The dichlorinated indole-3-acetic acids: 4,5-Cl₂-IAA, 4,6-Cl₂-IAA, 4,7-Cl₂-IAA, 5,6-Cl₂-IAA, 5,7-Cl₂-IAA and 6,7-Cl₂-IAA were synthesized and characterized by X-ray structure analysis to unambiguously identify the substances for bioassays required to establish structure activity relationships of auxins and their analogues. Straight-growth tests were performed on Avena sativa coleoptiles to correlate their auxin activity with molecular properties which could reveal information on the topology of the auxin binding site. Structure/activity correlations revealed that the 5,6-Cl₂-IAA molecule, by virtue of its size and shape, fits particularly well into the active site cavity of the receptor protein. The main contact of the substrate or inhibitor in the receptor active site via the carboxylic group determines their orientation in the active site cavity. As a consequence, the 5,6-substituted sites protrude into the widest part of the active site whereas the 7-, 4-, and 5-substituted sites are oriented towards the narrowest part of the active site. These topological parameters are in agreement with the high auxin activity of 5,6-Cl₂-IAA and the low activity of 4,7-Cl₂-IAA.

Original language	English (US)
Pages (from-to)	21-31
Number of pages	11
Journal	Plant Growth Regulation
Volume	27
Issue number	1
DOIs	https://doi.org/10.1023/A:1006031527789
State	Published - 1999

Bibliographical note

Funding Information:
This work was supported by grants no. 00980608 and 00980707 awarded by the Croatian Ministry of Science and Technology, by United States-Croatian Research Agreement no. JF202 and by U.S. Dept. of Energy grant DE-AI02-94ER20153. The help of K.C. Engvild (Risø National Laboratory, Roskilde, Denmark) who generously supplied samples of dichlo-rinated indole-3-acetic acids is gratefully acknowledged.

Keywords

Auxin
Avena sativa straight growth test
Biological activity
Dichlorinated indole-3-acetic acid
Structural characterization

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@article{0aefdd223a8147a0b208100c43779d79,

title = "Structural characterization and auxin properties of dichlorinated indole-3-acetic acids",

abstract = "The dichlorinated indole-3-acetic acids: 4,5-Cl2-IAA, 4,6-Cl2-IAA, 4,7-Cl2-IAA, 5,6-Cl2-IAA, 5,7-Cl2-IAA and 6,7-Cl2-IAA were synthesized and characterized by X-ray structure analysis to unambiguously identify the substances for bioassays required to establish structure activity relationships of auxins and their analogues. Straight-growth tests were performed on Avena sativa coleoptiles to correlate their auxin activity with molecular properties which could reveal information on the topology of the auxin binding site. Structure/activity correlations revealed that the 5,6-Cl2-IAA molecule, by virtue of its size and shape, fits particularly well into the active site cavity of the receptor protein. The main contact of the substrate or inhibitor in the receptor active site via the carboxylic group determines their orientation in the active site cavity. As a consequence, the 5,6-substituted sites protrude into the widest part of the active site whereas the 7-, 4-, and 5-substituted sites are oriented towards the narrowest part of the active site. These topological parameters are in agreement with the high auxin activity of 5,6-Cl2-IAA and the low activity of 4,7-Cl2-IAA.",

keywords = "Auxin, Avena sativa straight growth test, Biological activity, Dichlorinated indole-3-acetic acid, Structural characterization",

author = "Snje{\v z}ana Antoli{\'c} and Branka Salopek and Biserka Koji{\'c}-Prodi{\'c} and Volker Magnus and Cohen, {Jerry D.}",

note = "Funding Information: This work was supported by grants no. 00980608 and 00980707 awarded by the Croatian Ministry of Science and Technology, by United States-Croatian Research Agreement no. JF202 and by U.S. Dept. of Energy grant DE-AI02-94ER20153. The help of K.C. Engvild (Ris{\o} National Laboratory, Roskilde, Denmark) who generously supplied samples of dichlo-rinated indole-3-acetic acids is gratefully acknowledged.",

year = "1999",

doi = "10.1023/A:1006031527789",

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T1 - Structural characterization and auxin properties of dichlorinated indole-3-acetic acids

AU - Antolić, Snježana

AU - Salopek, Branka

AU - Kojić-Prodić, Biserka

AU - Magnus, Volker

AU - Cohen, Jerry D.

N1 - Funding Information: This work was supported by grants no. 00980608 and 00980707 awarded by the Croatian Ministry of Science and Technology, by United States-Croatian Research Agreement no. JF202 and by U.S. Dept. of Energy grant DE-AI02-94ER20153. The help of K.C. Engvild (Risø National Laboratory, Roskilde, Denmark) who generously supplied samples of dichlo-rinated indole-3-acetic acids is gratefully acknowledged.

PY - 1999

Y1 - 1999

N2 - The dichlorinated indole-3-acetic acids: 4,5-Cl2-IAA, 4,6-Cl2-IAA, 4,7-Cl2-IAA, 5,6-Cl2-IAA, 5,7-Cl2-IAA and 6,7-Cl2-IAA were synthesized and characterized by X-ray structure analysis to unambiguously identify the substances for bioassays required to establish structure activity relationships of auxins and their analogues. Straight-growth tests were performed on Avena sativa coleoptiles to correlate their auxin activity with molecular properties which could reveal information on the topology of the auxin binding site. Structure/activity correlations revealed that the 5,6-Cl2-IAA molecule, by virtue of its size and shape, fits particularly well into the active site cavity of the receptor protein. The main contact of the substrate or inhibitor in the receptor active site via the carboxylic group determines their orientation in the active site cavity. As a consequence, the 5,6-substituted sites protrude into the widest part of the active site whereas the 7-, 4-, and 5-substituted sites are oriented towards the narrowest part of the active site. These topological parameters are in agreement with the high auxin activity of 5,6-Cl2-IAA and the low activity of 4,7-Cl2-IAA.

AB - The dichlorinated indole-3-acetic acids: 4,5-Cl2-IAA, 4,6-Cl2-IAA, 4,7-Cl2-IAA, 5,6-Cl2-IAA, 5,7-Cl2-IAA and 6,7-Cl2-IAA were synthesized and characterized by X-ray structure analysis to unambiguously identify the substances for bioassays required to establish structure activity relationships of auxins and their analogues. Straight-growth tests were performed on Avena sativa coleoptiles to correlate their auxin activity with molecular properties which could reveal information on the topology of the auxin binding site. Structure/activity correlations revealed that the 5,6-Cl2-IAA molecule, by virtue of its size and shape, fits particularly well into the active site cavity of the receptor protein. The main contact of the substrate or inhibitor in the receptor active site via the carboxylic group determines their orientation in the active site cavity. As a consequence, the 5,6-substituted sites protrude into the widest part of the active site whereas the 7-, 4-, and 5-substituted sites are oriented towards the narrowest part of the active site. These topological parameters are in agreement with the high auxin activity of 5,6-Cl2-IAA and the low activity of 4,7-Cl2-IAA.

KW - Auxin

KW - Avena sativa straight growth test

KW - Biological activity

KW - Dichlorinated indole-3-acetic acid

KW - Structural characterization

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EP - 31

JO - Plant Growth Regulation

JF - Plant Growth Regulation

IS - 1

ER -

Structural characterization and auxin properties of dichlorinated indole-3-acetic acids

Abstract

Bibliographical note

Keywords

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