CAS: 6678-82-6; 1-Methyl-2,3,4,9-Tetrahydro-1H-Pyrido[3,4-B]Indole Hydrochloride

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tryptamine acetaldehyde tryptamine hyd°Chloride (R)-1-methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole harmane

📜色胺盐酸盐,乙醛 反应生成 Dl-盐酸胡秃子碱
参考文献:Monoamine Oxidase (Mao-N) Catalyzed Deracemization Of Tetrahydro-β-Carbolines: Substrate Dependent Switch In Enantioselectivity
标题:Monoamine Oxidase (Mao-N) Catalyzed Deracemization Of Tetrahydro-β-Carbolines: Substrate Dependent Switch In Enantioselectivity
摘要:The Tetrahydro-Beta-Carboline (Thbc) Ring System Is An Important Structural Motif Found In A Large Number Of Bioactive Alkaloid Natural Products. Herein We Report A Broadly Applicable Method For The Synthesis Of Enantiomerically Pure Beta-Carbolines Via A Deracemization Procedure Employing The D9 And D11 Variants Of Monoamine Oxidase From Aspergillus Niger (Mao-N) In Combination With A Nonselective Chemical Reducing Agent. Biotransformations Were Performed On A Preparative Scale,Leading To The Synthesis Of Optically Enriched Products In Excellent Enantiomeric Excess (E.E.; Up To 99%) And Isolated Yield (Up To 93%). Interestingly,A Switch In Enantioselectivity Associated With The Mao-N Variants Is Observed As The Nature Of The C-1 Substituent Of The Thbc Is Varied. Molecular Modeling Provided An Explanation For This Observation And Highlighted Key Active Site Residues Which Were Modified,Resulting In An Increase In (R)-Selectivity Associated With The Enzyme. These Results Provide Insight Into The Factors Which Influence The Selectivity Of The Mao-N Variants,And May Offer A Platform For Future Directed Evolution Projects Aimed Toward The Challenge Of Engineering (R)-Selective Amine Oxidase Biocatalysts.
DOI:10.1021/cs400724G