0000000000299874

AUTHOR

Marcel Reimann

showing 3 related works from this author

A new member of the fusaricidin family – structure elucidation and synthesis of fusaricidin E

2017

Two hitherto unknown fusaricidins were obtained from fermentation broths of three Paenibacillus strains. After structure elucidation based on tandem mass spectrometry and NMR spectroscopy, fusaricidin E was synthesized to confirm the structure and the suggested stereochemistry. The synthesis was based on a new strategy which includes an efficient access to the 15-guanidino-3-hydroxypentadecanoyl (GHPD) side chain from erucamide.

cyclodepsipeptidesStereochemistry010402 general chemistryTandem mass spectrometry01 natural sciencesFull Research Paperlcsh:QD241-441Paenibacilluslcsh:Organic chemistrySide chaintotal synthesislcsh:Sciencebiology010405 organic chemistryChemistryFamily structureOrganic Chemistrystructure elucidationTotal synthesisNuclear magnetic resonance spectroscopyfusaricidinsbiology.organism_classificationlipopeptides0104 chemical sciencesChemistryFermentationlcsh:QBeilstein Journal of Organic Chemistry
researchProduct

Acute and Repeated Treatment with 5-PAHSA or 9-PAHSA Isomers Does Not Improve Glucose Control in Mice

2018

Summary Fatty acid esters of hydroxylated fatty acids (FAHFAs) were discovered as a novel class of endogenous mammalian lipids whose profound effects on metabolism have been shown. In the current study, in vitro and in vivo the metabolic effects of two of these FAHFAs, namely palmitic acid-5- (or -9) -hydroxy-stearic acid (5- or 9-PAHSA, respectively) were profiled. In DIO mice fed with differentially composed low- or high-fat diets, acute and subchronic treatment with 5-PAHSA and 9-PAHSA alone, or in combination, did not significantly improve the deranged metabolic status. Neither racemic 5- or 9-PAHSA, nor the enantiomers were able to: (1) increase basal or insulin-stimulated glucose upta…

0301 basic medicinechemistry.chemical_classificationgeographymedicine.medical_specialtygeography.geographical_feature_categoryPhysiologyGlucose uptakeFatty acid030209 endocrinology & metabolismEndogenyCell BiologyMetabolismIsletmedicine.disease03 medical and health sciencesBasal (phylogenetics)030104 developmental biology0302 clinical medicineInsulin resistanceEndocrinologychemistryCell cultureInternal medicinemedicineMolecular BiologyCell Metabolism
researchProduct

Total Synthesis of Phenanthroindolizidine Alkaloids by Combining Iodoaminocyclization with Free Radical Cyclization

2016

A concise and modular synthesis of phenanthroindolizidine alkaloids was achieved by combining iodoaminocylization with a free radical cyclization approach. The route described allowed the preparation of (±)-tylophorine, (±)-antofine, and (±)-deoxypergularinine in six steps. When commercially available l-prolinol was used as a chiral building block, (S)-(+)-tylophorine was also synthesized in 49% yield and >99% ee over five linear steps.

IndolesMagnetic Resonance SpectroscopyPyrrolidinesFree RadicalsChemistry OrganicStereoisomerism010402 general chemistry01 natural sciencesRadical cyclizationStructure-Activity RelationshipAlkaloidsOrganic chemistry010405 organic chemistryChemistryOrganic ChemistryIndolizinesTemperatureTotal synthesisStereoisomerismNuclear magnetic resonance spectroscopyPhenanthrenesIsoquinolines0104 chemical sciencesCyclizationYield (chemistry)PhenanthrolinesThe Journal of Organic Chemistry
researchProduct