Synthesis, Absolute Configuration and Biological Activity of Both Enantiomers of 2-(5,6-Dichloro-3-indolyl)propionic Acid: New Dichloroindole Auxins.
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- KATAYAMA Masato
- Department of Chemistry, National Industrial Research Institute of Nagoya(NIRIN)
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- KATO Yasuhito
- Ageo & Fine Chemicals Research Laboratory, Nippon Kayaku Co. Ltd.
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- MARUMO Shingo
- Graduate School of Bioagricultural Sciences, Nagoya University
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Abstract
Racemic 2-(5,6-dichloro-3-indolyl)propionic acid (5,6-Cl2-2-IPA) was synthesized from 5,6-dichloro-indole-3-acetic acid (5,6-Cl2-IAA) by successive esterification, methoxycarbonylation, methylation, and double hydrolysis. The racemate was converted to the diastereomeric esters of (S)-(−)-1-phenylethyl alcohol. These were separated by HPLC into two optically active diastereomers and then hydrolyzed with p-TsOH to the optically active enantiomers of 5,6-Cl2-2-IPA. The absolute configurations of both the 5,6-Cl2-2-IPA enantiomers were determined by comparing the 1H-NMR spectra of their diastereomeric (S)-(−)-1-phenylethyl esters with those of the diastereomeric (S)-(−)-1-phenylethyl esters of 2-(3-indolyl)propionic acid (2-IPA) whose absolute configurations are already known.<br> There was no essential difference between (S)-(+)- and (R)-(−)-5,6-Cl2-2-IPA in hypocotyl growth-inhibiting activity toward Chinese cabbage, but their inhibitory activities were stronger than that of the potent mother auxin, 5,6-Cl2-IAA. No essential difference in the coleoptile elongating activity of Avena sativa was apparent for the enantiomers, this activity being about one-third that of 5,6-Cl2-IAA.
Journal
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- Bioscience, Biotechnology, and Biochemistry
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Bioscience, Biotechnology, and Biochemistry 65 (2), 270-276, 2001
Japan Society for Bioscience, Biotechnology, and Agrochemistry
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Keywords
Details 詳細情報について
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- CRID
- 1390282681447517312
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- NII Article ID
- 110002680253
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- NII Book ID
- AA10824164
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- COI
- 1:CAS:528:DC%2BD3MXhslKgt7s%3D
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- ISSN
- 13476947
- 09168451
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- NDL BIB ID
- 5696636
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- PubMed
- 11302158
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- Abstract License Flag
- Disallowed