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Molecular properties of 4-substituted indole-3-acetic acids affecting pea pericarp elongation

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Abstract

Pea (Pisum sativum L.) fruit naturally contain the auxins, indole-3-acetic acid (IAA) and 4-chloroindole-3-acetic acid (4-Cl-IAA). However, only 4-Cl-IAA can substitute for the seeds in maintaining pea fruit growth in planta. The importance of the substituent at the 4-position of the indole ring was tested by comparing the molecular properties of 4-X-IAA (X = H, Me, Et, F, or Cl) and their effect on the elongation of pea pericarps in planta. Structure-activity is discussed in terms of structural data derived from X-ray analysis, computed conformations in solution, semiempirical shape and bulk parameters, and experimentally determined lipophilicities and NH-acidities. The size of the 4-substituent, and its lipophilicity are associated with growth promoting activity of pea pericarp, while there was no obvious relationship with electromeric effects.

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Authors and Affiliations

  1. Department of Agricultural, Food, and Nutritional Science, Plant Physiology and Molecular Biology Research Group, University of Alberta, Edmonton, Alberta, Canada, T6G 2P5

    Dennis M. Reinecke & Jocelyn A. Ozga

  2. Department of Plant Biology, University of Maryland, College Park, MD, 20742, U.S.A

    Nebojša Ilić

  3. Rudđer Bošković Institute, Bijenička cesta 54, 10001, Zagreb, Croatia

    Volker Magnus & Biserka kojić-Prodić

Authors
  1. Dennis M. Reinecke
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  2. Jocelyn A. Ozga
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  3. Nebojša Ilić
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  4. Volker Magnus
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  5. Biserka kojić-Prodić
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Reinecke, D.M., Ozga, J.A., Ilić, N. et al. Molecular properties of 4-substituted indole-3-acetic acids affecting pea pericarp elongation. Plant Growth Regulation 27, 39–48 (1999). https://doi.org/10.1023/A:1006013216818

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