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Publikationen - Natur- und Wirkstoffchemie

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Publikation

Kolbe, A.; Fuchs, P.; Porzel, A.; Baumeister, U.; Kolbe, A.; Adam, G.; Synthesis and crystal structure of [26,27-2H6] 24-epi-cathasterone J. Chem. Soc., Perkin Trans. 1 2002, 2022-2027, (2002) DOI: 10.1039/B203323B

The first synthesis of [26,27-2H6]24-epi-cathasterone 8via (20S)-3β-acetoxy-6,6-(ethylenedioxy)-20-formyl-5α-pregnane 5 starting from stigmasterol is described. The aldehyde 5 was alkylated with lithium butyldimethyl-(E)-2,3-dimethyl[3,3,3,4,4,4-2H6]butenylaluminate 6 prepared from 3-[2H3]methyl[4,4,4-2H3]but-1-yne. The structure was determined using spectral data and X-ray crystallographic analysis.
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.
Bücher und Buchkapitel

Faust, J.; Wrenger, S.; Reinhold, D.; Kähne, T.; Lorey, S.; Stöckel-Maschek, A.; Brandt, W.; Mrestani-Klaus, C.; Stiebitz, B.; Fuchs, P.; Ansorge, S.; Neubert, K.; Down regulation of T-cell activation by synthetic dipeptidyl peptidase IV inhibitors with the N.terminal MXP sequence (Bendetti, E. & Predone, C., eds.). 750-751, (2002)

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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

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.
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