Modulating chitin synthesis in marine algae with iminosugars obtained by SmI2 and FeCl3-mediated diastereoselective carbonyl ene reaction

Author:

Holzwarth Marcel1,Ludwig Jan2ORCID,Bernz Alexander1,Claasen Birgit1,Majoul Asma2,Reuter Julia2,Zens Anna1,Pawletta Brigitte3,Bilitewski Ursula3,Weiss Ingrid M.245ORCID,Laschat Sabine1ORCID

Affiliation:

1. Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany

2. Institut für Biomaterialien und Biomolekulare Systeme, Universität Stuttgart, Pfaffenwaldring 57, D-70569 Stuttgart, Germany

3. Abteilung Chemische Biologie, Helmholtz-Zentrum für Infektionsforschung, Inhoffenstr. 7, D-38124 Braunschweig, Germany

4. AMICA – Stuttgart Research Focus (SRF), University of Stuttgart, Pfaffenwaldring 32, 70569 Stuttgart, Germany

5. Suttgart Research Center Systems Biology (SRCSB), University of Stuttgart, Stuttgart 70569, Germany

Abstract

Samarium iodide was employed in a stereoselective cyclization, starting from enantiopure amino acids towards iminosugar analogues, which influence chitin synthesis in the eukaryotic algae Thalassiosira as quantified in vivo via light microscopy.

Funder

European Regional Development Fund

Carl-Zeiss-Stiftung

Deutsche Forschungsgemeinschaft

Ministerium für Wissenschaft, Forschung und Kunst Baden-Württemberg

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

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