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

Plant Growth Regulation

Volumn 27, Issue 1, 1999, Pages 21-31

  Antolić, Snježana ^a   Salopek, Branka ^a   Kojić Prodić, Biserka ^a   Magnus, Volker ^a   Cohen, Jerry D ^b  

^a RUDER BO KOVI INSTITUTE   (Croatia)

^b AGRICULTURAL RESEARCH SERVICE   (United States)

Author keywords

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

Indexed keywords

EID: 0032975855     PISSN: 01676903     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1006031527789     Document Type: Article

References (40)

1. Ahmad A, Andersen AS and Engvild K (1987) Rooting, growth and ethylene evolution of pea cuttings in response to chloroindole auxins. Physiol Plant 69: 137-140
2. Allen FH and Kennard O (1993) 3D Search and research using the Cambridge Structural Database. Automation News 8: 131-137
3. Antolić S, Kojić-Prodić B, Tomić S, Nigović B, Magnus V and Cohen JD (1996) Structural studies on monofluorinated derivatives of the phytohormone indole-3-acetic acid (Auxin). Acta Crystallogr B52: 651-661
4. 14C-labeled halogen substituted indole-3-acetic acids. Journal of Labelled Compounds and Radiopharmaceuticals 22: 279-285
5. Bernstein J, Davies RE, Shimoni L and Chang N-L (1995) Patterns in hydrogen bonding: Functionality and graph set analysis in crystals. Angew Chem Int Ed Engl 34: 1555-1573
6. Böttger M, Engvild KC and Soll H (1978) Growth of Avena coleoptiles and pH drop of protoplast suspensions induced by chlorinated indoleacetic acids. Planta 140: 89-92
7. Catalan J and de Paz JLG (1997) The molecular geometry of indole. J Mol Struct (Theochem) 401: 189-192
8. Gandar JC and Nitsch JP (1967) Isolement de l'ester méthylique d'un acide chloro-3-indolylacétique à partir de graines immatures de Pois, Pisum sativum L. C R Acad Sci, Paris, Ser D 265: 1795-1798
9. Engvild KC (1977) Preparation of chlorinated 3-indolylacetic acids. Acta Chem Scand, Sect B 31: 338-339
10. Engvild KC (1978) Substituted indoleacetic acids tested in tissue cultures. Physiol Plant 44: 345-346
11. Fox SW and Bullock MW (1951) Synthesis of indoleacetic acid from glutamic acid and a proposed mechanism for the conversion. J Am Chem Soc 73: 2754-2755
12. Frenz BA & Associates, Inc. (1982) SDP/VAX Structure Determination Package. Texas, U.S.A.: College Station
13. Hatano T, Katayama M and Marumo S (1987) 5,6-Dichloroindole-3-acetic acid as a potent auxin: its synthesis and biological activity. Experientia 43: 1237-1239
14. Hoffmann OL, Fox SW and Bullock MW (1952) Auxin-like activity of systematically substituted indoleacetic acids. J Biol Chem 196: 437-441
15. Johnson CK (1976) ORTEPII. Report ORNL-5138. Tennessee, U.S.A.: Oak Ridge National Laboratory
16. Katekar G (1979) Auxins: On the nature of the receptor site and molecular requirements for auxin activity. Phytochemistry 18: 223-233
17. Katekar GF and Geissler AE (1982) Auxins II: The effect of chlorinated indolylacetic acids on pea stems. Phytochemistry 21: 257-260
18. Klyne W and Prelog V (1960) Description of steric relationships across single bonds. Experientia 16: 521-523
19. Kojić-Prodić B, Nigović B, Tomić S, Ilić N, Magnus V, Giba Z, Konjević R and Duax WL (1991) Structural studies on 5-(n-alkyl)-substituted derivatives of the plant hormone indole-3-acetic acid. Acta Crystallogr Sect B 47: 1010-1019
20. Larsen P (1961) Biological determination of natural auxin. In: Ruhland W (ed) Encyclopedia of Plant Physiology, Vol. 14. Berlin: Springer-Verlag, pp 521-582
21. Libbenga KR, Maan AC, van der Linde PCG and Mennes AM (1986) Hormones, receptors and cellular interactions in plants. In: Chadwick CM and Garrod DR (eds) Cambridge: Cambridge University Press, Chapter 1, p 1
22. Lüthen H and Böttger M (1988) Kinetics of proton secretion and growth in maize roots: Action of various plant growth effectors. Plant Science (Ireland) 54: 37-43
23. Marumo S, Hattori H, Abe H and Munakata K (1968) Isolation of a novel auxin, methyl 4-chloroindoleacetate from immature seeds of Pisum sativum. Agr Biol Chem 32: 117-118
24. Mitchell JW and Livingston GA (1968) Methods of Studying Plant Hormones and Growth-Regulating Substances, Agriculture Handbook No. 336. Washington, D.C.: Agricultural Research Service, United States Department of Agriculture
25. Nigović B (1992) PhD Thesis. Zagreb, Croatia: University of Zagreb
26. Nigović B, Kojić-Prodić B, Antolić S, Tomić S, Puntarec V and Cohen JD (1996) Structural studies on monohalogenated derivatives of the phytohormone indole-3-acetic acid (Auxin). Acta Crystallogr B52: 332-343
27. Porter WL and Thimann KV (1965) Molecular requirements for auxin action - I. Halogenated indoles and indoleacetic acids. Phytochemistry 4: 229-243
28. Salcher O and Lingens F (1978) Biosynthese von Pyrrolnitrin. Nachweis von 3-Chloranthranilsäure und 7-Chlorindolessigsäure im Kulturmedium von Pseudomonas aureofaciens. Tetrahedron Lett 34: 3101-3102
29. Sell HM, Wittwer SH, Rebstock TL and Redemann CT (1952) Comparative stimulation of parthenocarpy in the tomato by various indole compounds. Plant Physiol 28: 481-487
30. Sheldrick GM (1976) SHELX 76. Program for Crystal Structure Determination. England: Univ. of Cambridge
31. Sheldrick GM (1990) Phase annealing in SHELX-90: Direct methods for larger structures. Acta Cryst A46: 467-473
32. Sheldrick GM (1997) SHELX L-97. Program for the Refinement of Crystal Structures. Germany: Univ of Göttingen
33. Slovin JP (1997) Phytotoxic conjugates of indole-3-acetic acid: Potential agents for biochemical selection of mutants in conjugate hydrolysis. Plant Growth Regulation 21: 215-221
34. Spek AL (1982) The EUCLID package. In: Sayre D (ed) Computation Crystallography. Oxford: Clarendon Press, p 528
35. Spek AL (1993) HELENA Program for Data Reduction. The Netherlands: University of Utrecht
36. Stenlid G and Engvild KC (1987) Effects of chlorosubstituted indoleacetic acids on root growth, ethylene and ATP formation. Physiol Plant 70: 109-113
37. Tomić S, van Duijneveldt FB, Kroon-Batenburg LM and Kojić-Prodić B (1995) Molecular mechanics and SCF MO conformational analysis of indole-3-acetic acid phytohormone (Auxin). Croat Chem Acta 68: 205-214
38. Venis AM and Napier RM (1995) Auxin receptors and auxin binding proteins. Critical Reviews in Plant Sciences 14: 27-47
39. Yoshimatsu K, Hatano T, Katayama M, Marumo S, Kamada H and Shimomura K (1990) IAA derivative induced tropane alkaloid production in root cultures of a Duboisia hybrid. Phytochemistry 29: 3535-3528
40. Zažímalová E and Kutáček M (1985) Auxin-binding site in wheat shoots: Interactions between indol-3-ylacetic acid and its halogenated derivatives. Biologia Plantarum (Praha) 27: 114-118