Inverted Binding of Non-natural Substrates in Strictosidine Synthase Leads to a Switch of Stereochemical Outcome in Enzyme-Catalyzed Pictet–Spengler Reactions-Reference-Cited by-同舟云学术

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Inverted Binding of Non-natural Substrates in Strictosidine Synthase Leads to a Switch of Stereochemical Outcome in Enzyme-Catalyzed Pictet–Spengler Reactions

Published:2020-01-07 Issue:2 Volume:142 Page:792-800
ISSN:0002-7863
Container-title:Journal of the American Chemical Society
language:en
Short-container-title:J. Am. Chem. Soc.

Author:

Eger Elisabeth¹,Simon Adam²^ORCID,Sharma Mahima³^ORCID,Yang Song²,Breukelaar Willem B.¹,Grogan Gideon³^ORCID,Houk K. N.²^ORCID,Kroutil Wolfgang¹^ORCID

Affiliation:

1. Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz, Austria

2. Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States

3. Department of Chemistry, University of York, Heslington, York YO15 5DD, U.K.

Funder

Austrian Science Fund

National Institute of General Medical Sciences

Biotechnology and Biological Sciences Research Council

Publisher

American Chemical Society (ACS)

Subject

Colloid and Surface Chemistry,Biochemistry,General Chemistry,Catalysis

Link

http://pubs.acs.org/doi/pdf/10.1021/jacs.9b08704

Reference63 articles.

1. Natural isoquinoline alkaloids: binding aspects to functional proteins, serum albumins, hemoglobin, and lysozyme

2. β-Carboline Alkaloids: Biochemical and Pharmacological Functions

3. Über die Bildung von Isochinolin‐derivaten durch Einwirkung von Methylal auf Phenyl‐äthylamin, Phenyl‐alanin und Tyrosin

4. Enantiospecific Formation of Trans 1,3-Disubstituted Tetrahydro-β-carbolines by the Pictet−Spengler Reaction and Conversion of Cis Diastereomers into Their Trans Counterparts by Scission of the C-1/N-2 Bond

5. Enhancing the yield and diastereoselectivity of the Pictet-Spengler reaction: A highly efficient route to Cis-1,3-disubstituted tetrahydro-β-carbolines

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