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  Biocatalytic asymmetric formation of tetrahydro-beta-carbolines

Bernhardt, P., Usera, A. R., & O'Connor, S. E. (2010). Biocatalytic asymmetric formation of tetrahydro-beta-carbolines. Tetrahedron Letters, 51(33), 4400-4402. doi:10.1016/j.tetlet.2010.06.075.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0002-AEA7-E Version Permalink: https://hdl.handle.net/21.11116/0000-0009-3D3E-F
Genre: Journal Article

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SOC027.pdf (Publisher version), 694KB
 
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SOC027s1.pdf (Supplementary material), 10MB
 
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 Creators:
Bernhardt, Peter1, Author
Usera, Aimee R.1, Author
O'Connor, Sarah E.1, Author           
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1external, ou_persistent22              

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Free keywords: PICTET-SPENGLER REACTIONS; STRICTOSIDINE SYNTHASE; ALKALOID BIOSYNTHESIS; ENZYME; EXPRESSION; CATALYSIS; SEQUENCEChemistry;
 Abstract: Strictosidine synthase triggers the formation of strictosidine from tryptamine and secologanin, thereby generating a carbon-catbon bond and a new stereogenic center Strictosidine contains a tetrahydro-beta-carboline moiety an important N-heterocyclic framework found in a range of natural products and synthetic pharmaceuticals Stereoselective methods to produce tetrahydro-B-carboline enantiomers are greatly valued We report that strictosidine synthase from Ophiorrhiza pumila utilizes a range of simple achiral aldehydes and substituted tryptamines to form highly enantioenriched (ee >98%) tetrahydro-beta-carbolines via a Pictet-Spengler reaction This is the first example of aldehyde substrate promiscuity in the strictosidine synthase family of enzymes and represents a first step toward developing a general biocatalytic strategy to access chiral tetrahydro-beta-carbolines (C) 2010 Elsevier Ltd All rights reserved

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Language(s): eng - English
 Dates: 2010
 Publication Status: Issued
 Pages: 3
 Publishing info: -
 Table of Contents: -
 Rev. Type: -
 Identifiers: Other: SOC027
DOI: 10.1016/j.tetlet.2010.06.075
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Title: Tetrahedron Letters
  Other : Tetrahedron Lett.
Source Genre: Journal
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Publ. Info: Oxford : Pergamon
Pages: - Volume / Issue: 51 (33) Sequence Number: - Start / End Page: 4400 - 4402 Identifier: ISSN: 0040-4039
CoNE: https://pure.mpg.de/cone/journals/resource/954925448772