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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

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Volume 71, Issue 12 (Dec 2016)

Issues

Structure elucidation and synthesis of hydroxylated isatins from Streptomycetes

Khaled A. Shaaban
  • Institute of Organic and Biomolecular Chemistry, University of Göttingen, D-37077 Göttingen, Germany
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/ Mohamed Shaaban
  • Institute of Organic and Biomolecular Chemistry, University of Göttingen, D-37077 Göttingen, Germany
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/ Vimal Nair
  • Institute of Organic and Biomolecular Chemistry, University of Göttingen, D-37077 Göttingen, Germany
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/ Imelda Schuhmann
  • Institute of Organic and Biomolecular Chemistry, University of Göttingen, D-37077 Göttingen, Germany
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/ Hnin Yu Win
  • Institute of Organic and Biomolecular Chemistry, University of Göttingen, D-37077 Göttingen, Germany
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/ Lei Lei
  • Institute of Organic and Biomolecular Chemistry, University of Göttingen, D-37077 Göttingen, Germany
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/ Birger Dittrich / Elisabeth Helmke / Anja Schüffler / Hartmut Laatsch
  • Corresponding author
  • Institute of Organic and Biomolecular Chemistry, University of Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany
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Published Online: 2016-10-18 | DOI: https://doi.org/10.1515/znb-2016-0143

Abstract

Chemical investigation of terrestrial and marine streptomycete isolates led to the identification of two new natural pigments, namely, 6-hydroxyisatin (3) and 6-hydroxy-5-methoxyisatin (4). Additionally, the strains delivered numerous known compounds, among them Nβ-acetyltryptamine, N-acetyltyramine, phenylacetamide, N-(2-phenethyl)acetamide, 1-acetyl-β-carboline, tyrosol, 2′-deoxyadenosine, 2′-deoxythymidine, anthranilic acid, 2′-deoxyuridine, indolyl-3-acetic acid, indolyl-3-carboxylic acid, and p-hydroxybenzoic acid. The isatin structures were deduced by NMR and mass studies and further confirmed by synthesis and by X-ray diffraction of the isomeric 5-hydroxy-6-methoxyisatin (5).

This article offers supplementary material which is provided at the end of the article.

Keywords: isatins; natural pigments; streptomycetes; synthesis; X-ray diffraction

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About the article

Received: 2016-06-08

Accepted: 2016-07-13

Published Online: 2016-10-18

Published in Print: 2016-12-01


Citation Information: Zeitschrift für Naturforschung B, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2016-0143.

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