6533b821fe1ef96bd127c297
RESEARCH PRODUCT
A facile chemoenzymatic approach: one-step syntheses of monoterpenoid indole alkaloids.
Joachim StöckigtJoachim StöckigtLiuqing YangLiuqing YangHongbin ZouHuajian ZhuYongping YuLiang Zhangsubject
TryptamineModels MolecularRauvolfiaStrictosidine synthaseStereochemistryOne-StepBiochemistryRauwolfiachemistry.chemical_compoundCarbon-Nitrogen LyasesSecologanin Tryptamine AlkaloidsVinca AlkaloidsAza CompoundsbiologyMolecular StructureOrganic ChemistryGeneral Chemistrybiology.organism_classificationEnzymes ImmobilizedSecologanin Tryptamine AlkaloidsRecombinant ProteinschemistryBiocatalysisStrictosidinebiology.proteinBiocatalysisSecologanindescription
Facile chemoenzymatic syntheses of cytotoxic monoterpenoid indole alkaloids with novel skeletons and multiple chiral centers are described. Synthesis of these alkaloids was achieved by a simple one-step reaction using strictosidine and 12-aza-strictosidine as the key intermediates. Strictosidines were prepared by coupling of secologanin with tryptamine and 7-aza-tryptamine, respectively, using the immobilized recombinant Rauvolfia strictosidine synthase. A detailed stereochemical analysis is presented herein. The results provide an opportunity for a chemoenzymatic approach that leads to an increased diversification of complex alkaloids with improved structures and activities.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2010-09-28 | Chemistry, an Asian journal |