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Journal / Buchreihe / Preprint-Server Nach Häufigkeit alphabetisch sortiert: BMC Genomics
Journal / Buchreihe / Preprint-Server Nach Häufigkeit alphabetisch sortiert: Chromatographia
Autor Nach Häufigkeit alphabetisch sortiert: Gabel, A
Autor Nach Häufigkeit alphabetisch sortiert: Wasternack, C
Autor Nach Häufigkeit alphabetisch sortiert: Wasternack, C.
Journal / Buchreihe / Preprint-Server Nach Häufigkeit alphabetisch sortiert: Curr Opin Plant Biol.
Journal / Buchreihe / Preprint-Server Nach Häufigkeit alphabetisch sortiert: Plant Signal Behav
Journal / Buchreihe / Preprint-Server Nach Häufigkeit alphabetisch sortiert: Z. Naturforsch.
Journal / Buchreihe / Preprint-Server Nach Häufigkeit alphabetisch sortiert: Plant and Cell Physiol.
Journal / Buchreihe / Preprint-Server Nach Häufigkeit alphabetisch sortiert: Tetrahedron
Autor Nach Häufigkeit alphabetisch sortiert: Kwaśniewska, D.
Journal / Buchreihe / Preprint-Server Nach Häufigkeit alphabetisch sortiert: Eur. J. Plant Pathol.
Autor Nach Häufigkeit alphabetisch sortiert: Kramell, R.
Autor Nach Häufigkeit alphabetisch sortiert: Grosse, I.
Erscheinungsjahr: 1999
Erscheinungsjahr: 1997
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- FEBS Lett. (5)
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- Kramell, R. (2)
- Miersch, O. (2)
- Schneider, G. (2)
- Wasternack, C. (2)
- Beale, M. H. (1)
- Gaskin, P. (1)
- Koda, Y. (1)
- Sessions, R. (1)
- Ward, J. L. (1)
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Kramell, R.; Miersch, O.; Schneider, G.; Wasternack, C.; Liquid chromatography of jasmonic acid amine conjugates Chromatographia 49, 42-46, (1999) DOI: 10.1007/BF02467185
Racemic jasmonic acid (3R,7R/3S,7S)-(±)-JA) was chemically conjugated with different biogenic amines originating from aliphatic and aromatic α-amino acids by decarboxylation. The resulting isomeric compounds were subjected to reversed-phase high-performance liquid chromatography (HPLC) and to HPLC on the chiral stationary phases Chiralpak AS and Nucleodex β-PM. Under reversed-phase conditions, all the homologous amine derivatives tested could be separated from each other except the JA-conjugates containing 2-phenyl-ethylamine and 3-methylbutylamine. On both chiral supports the (3R,7R)-(−)-JA conjugates eluted earlier than those of the enantiomeric counterpart (3S,7S)-(+)-JA. On Chiralpak AS all the isomers studied could be separated to baseline with a mobile phase containingn-hexane and 2-propanol. The calculated resolution factors were between 1.80 and 4.17. The pairs of isomers were also chromatographed on the cyclodextrin stationary phase Nucleodex β-PM with methanol-triethylammonium acetate buffer as mobile phase. Under these conditions resolution factors were between 0.74 and 1.29. The individual isomers were chiroptically characterized by measurement of their circular dichroism.
Ward, J. L.; Gaskin, P.; Beale, M. H.; Sessions, R.; Koda, Y.; Wasternack, C.; Molecular modelling, synthesis and biological activity of methyl 3-methyljasmonate and related derivatives Tetrahedron 53, 8181-8194, (1997) DOI: 10.1016/S0040-4020(97)00485-7
Methyl 3-methyljasmonate was synthesised from methyl jasmonate via methyl 3,7-dehydrojasmonate. Molecular modelling predicted an increase in the proportion of cis-orientated side-chains for equilibrated 3-methyl-substituted jasmonate. The synthetic 3-methyljasmonate was shown by gc-ms analysis to equilibrate to a 2:1 ratio of isomers, which appeared from the NMR spectra to comprise mainly the cis-isomer. Surprisingly, both 3,7-dehydro- and 3-methyl-derivatives were inactive in four well established jasmonate bioassays. Methyl-2-methyljasmonate was synthesised and also found to be inactive. Methyl 4,5-dehydrojasmonate was prepared, via the 5-diazo derivative. Both of these compounds have low activity. Our results are discussed with reference to previous knowledge of jasmonate structure-activity relationships and indicate that there are stringent steric demands in jasmonate-receptor interactions.
Kramell, R.; Schneider, G.; Miersch, O.; Chiral separation of amide conjugates of jasmonic acid by liquid chromatography Chromatographia 45, 104-108, (1997) DOI: 10.1007/BF02505545
Synthetic amide conjugates of (−)-jasmonic acid and its (+)-enantiomer were resolved by means of chiral liquid chromatography. The diastereomeric pairs prepared by chemical reaction of (±)-jasmonic acid with a series of (S)- or (R)-amino acids and with some (S)-amino acid alcohols were completely separated on Chiralpak AS using a mixture of n-hexane/2-propanal as mobile phase. The retention data indicate that the (−)-jasmonic acid conjugates eluted faster than those of the (+)-enantiomer, independent on the configuration of the bound amino acid. Likewise, enantiomeric derivatives of (±)-jasmonic acid and non-chiral amino acids were completely separated on the chiral stationary phase and showed the same elution sequence. The resolution factors,Rs, were found to range between 1.13 and 6.64. The separated compounds were chiropatically analyzed by measurement of the circular dichroism.