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Publikation

Schneider, G.; Fuchs, P.; Schmidt, J.; Evidence for the direct 2β‐ and 3β‐hydroxylation of [2H2]GA20‐13‐O‐[6′‐2H2]glucoside in seedlings of Phaseolus coccineus Physiol. Plant. 116, 144-147, (2002) DOI: 10.1034/j.1399-3054.2002.1160202.x

[17‐2H2]GA20‐13‐O‐[6′‐2H2]glucoside was synthesized and applied to seedlings of Phaseolus coccineus L. After incubation for 72 h the conjugate metabolites were purified and shown by LC‐ESI‐tandem‐MS and GC‐MS to be [17‐2H2]GA1‐13‐O‐[6′‐2H2]glucoside and [17‐2H2]GA29‐13‐O‐[6′‐2H2]glucoside. This is the first evidence for the conversion of intact GA‐O‐glucosides, and represents an additional metabolic pathway of the gibberellin metabolism in P. coccineus L. The results indicate that intact GA‐O‐glucosides are accepted by 2‐ and 3‐oxidases in the plant.
Publikation

Kolbe, A.; Kramell, R.; Porzel, A.; Schmidt, J.; Schneider, G.; Adam, G.; Syntheses of Dexamethasone Conjugates of the Phytohormones Gibberellin A3 and 24-Epicastasterone Collect. Czech. Chem. Commun. 67, 103-114, (2002) DOI: 10.1135/cccc20020103

The syntheses of N-[10-(9α-fluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxamido)decyl]gibberellamide (7) and 6-[({N-[10-(9α-fluoro-11β,17α-dihydroxy- 16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxamido)decyl]carbamoyl}methoxy)imino]-24-epicastasterone (10) are described. [(Benzotriazol-1-yl)oxy]bis(pyrrolidin-1-yl)methylium hexafluorophosphate (HBPyU) was used as the coupling agent for the reaction of gibberellic acid as well as of 24-epicastasterone-O-(carboxymethyl)oxime with N-(10-aminodecyl)- 9α-fluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxamide (4). The gibberellic acid conjugate 7 was also synthesised by the coupling of succinimidyl gibberellate 6 with amine 4.
Publikation

Schneider, G.; Koch, M.; Fuchs, P.; Schmidt, J.; Identification of metabolically formed glucosyl conjugates of [17-D2]-GA34 Phytochem. Anal. 11, 232-235, (2000) DOI: 10.1002/1099-1565(200007/08)11:4<232::AID-PCA525>3.0.CO;2-F

After application of [17‐D2]‐GA34 to seedlings of Phaseolus coccineus L. cv. Prizewinner, both metabolically formed conjugates [17‐D2]‐GA34‐2‐O‐glucoside and [17‐D2]‐GA34‐glucosyl ester could be established structurally. The identification was based on data from GC‐MS as well as LC‐ESI‐tandem MS (negative ions) techniques (daughter ion scan, parent ion scan, selected ion monitoring, selected reaction monitoring), and NMR studies.
Publikation

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.
Publikation

Kramell, R.; Porzel, A.; Miersch, O.; Schneider, G.; Wasternack, C.; Chromatographic resolution of peptide-like conjugates of jasmonic acid and of cucurbic acid isomers J. Chromatogr. A 847, 103-107, (1999) DOI: 10.1016/S0021-9673(99)00335-0

The chiral separation of peptide-like conjugates of jasmonic acid and of cucurbic acid isomers was investigated by liquid chromatography on Chiralpak AS and Nucleodex β-PM. The retention sequences reflect distinct chromatographic properties with respect to the chirality of the jasmonic acid part or of the cucurbic acid isomers. The chromatographic behaviour of the amide conjugates on a reversed-phase C18 column provides evidence for the resolution of diastereomeric conjugates depending on the chirality of both constituents of the conjugate molecule. The chromatographic procedures are suitable for the analytical and preparative separation of such conjugates.
Publikation

Kramell, R.; Porzel, A.; Miersch, O.; Schneider, G.; Analysis of synthetic isoleucine conjugates of cucurbic acid isomers by liquid chromatography Phytochem. Anal. 10, 82-87, (1999) DOI: 10.1002/(SICI)1099-1565(199903/04)10:2<82::AID-PCA448>3.0.CO;2-K

Conjugates of 3,7‐trans cucurbic acid isomers with either (S )‐ or (R )‐isoleucine were synthesised from the diastereomeric conjugate of (3R , 7R )‐jasmonic acid and (3S , 7S )‐jasmonic acid by sodium borohydride reduction. The resulting diastereomers were characterised by nuclear magnetic resonance spectra. The authentic substances were subjected to liquid chromatography using a reversed‐phase C18 matrix and the chiral stationary phase Chiralpak AS. For all (6RS )‐hydroxy epimeric pairs, a baseline separation could be observed. The elution sequences obtained indicate that the 3,6‐trans oriented epimers with (S )‐isoleucine elute prior to the 3,6‐cis configured individuals independent of the mode of chromatography. In contrast, the elution pattern of the conjugates containing (R )‐isoleucine was reversed on the chiral stationary phase. The epimers with a 3,6‐cis configured hydroxy group and the acid side chain eluted faster than those with the 3,6‐trans configuration. The chromatographic conditions described are suitable for resolving mixtures of isomeric N‐(cucurbinoyl)‐isoleucines in order to assign their stereochemistry and to obtain chiral reference materials on a preparative scale.
Bücher und Buchkapitel

Kramell, R.; Porzel, A.; Miersch, O.; Schneider, G.; Characterization of Isoleucine Conjugates of Cucurbic Acid Isomers by Reversed-Phase and Chiral High-Performance Liquid Chromatography 77-78, (1998)

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Publikation

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.
Publikation

Fuchs, P.; Porzel, A.; Schneider, G.; Partial Synthesis of [1β,2α,17,17-D4] Gibberellin A1 J. Prakt. Chem. 339, 448-452, (1997) DOI: 10.1002/prac.19973390178

An efficient route for an alternative synthesis of gibberllin A1 from gibberellin A3 is described. Based on iodolactonisation the method provides access to gibberellin A1 labeled by deuterium with both high incorporation of the isotope and high stereoselectity at the positions 1β and 2α. The additional deuterium labeling at C‐17 was introduced via the corresponding 16‐norketone resulting in [1β,2α,17,17‐D4] gibberellin A1.
Publikation

Kramell, R.; Atzorn, R.; Schneider, G.; Miersch, O.; Brückner, C.; Schmidt, J.; Sembdner, G.; Parthier, B.; Occurrence and identification of jasmonic acid and its amino acid conjugates induced by osmotic stress in barley leaf tissue J. Plant Growth Regul. 14, 29-36, (1995) DOI: 10.1007/BF00212643

The effect of osmotically active substances on the alteration of endogenous jasmonates was studied in barley (Hordeum vulgare L. cv. Salome) leaf tissue. Leaf segments were subjected to solutions of d-sorbitol, d-mannitol, polyethylene glycol 6000, sodium chloride, or water as a control. Alterations of endogenous jasmonates were monitored qualitatively and quantitatively using immunoassays. The structures of jasmonates isolated were determined on the basis of authentic substances by capillary gas chromatography-mass spectrometry. The stereochemistry of the conjugates was confirmed by high performance liquid chromatography with diastereoisomeric references. In barley leaves, jasmonic acid and its amino acid conjugates, for example, with valine, leucine, and isoleucine, are naturally occurring jasmonates. In untreated leaf segments, only low levels of these native jasmonates were found. After treatment of the leaf tissues with sorbitol, mannitol, as well as with polyethylene glycol, an increase of both jasmonic acid and its conjugates could be observed, depending on the stress conditions used. In contrast, salt stress was without any stimulating effect on the levels of endogenous jasmonates. From barley leaf segments exposed to sorbitol (1m) for 24 h, jasmonic acid was identified as the major accumulating compound. Jasmonic acid-amino acid conjugates increased likewise upon stress treatment.
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