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    Identification, synthesis, and conformation of tri- and tetrathiacycloalkanes from marine bacteria.

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    Authors
    Sobik, Paul
    Grunenberg, Jörg
    Böröczky, Katalin
    Laatsch, Hartmut
    Wagner-Döbler, Irene
    Schulz, Stefan
    Issue Date
    2007-05-11
    
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    Abstract
    Seven new cyclic natural polysulfides 1-7 were identified in extracts of two bacterial Cytophaga strains (CFB-phylum) isolated from biofilms from the North Sea. Their structures are based on mono- and dimeric-cyclization products of 2-methylpropane-1,2-dithiol 8, which was also present in the extract in trace amounts. The structures were deduced by analysis of their mass spectra and confirmed by synthesis. The 1H NMR spectra of some these compounds suggested a high flexibility of the trithiepane and tetrathiocane systems. Therefore, their conformation was further analyzed by DFT calculations and dynamic NMR spectroscopy. While thiepane 4 possesses a twist-chair lowest energy conformation, its isomers 2 and 3 adopt a chairlike conformation, as does the tetrathiocane 5. In contrast, tetrathiocane 6 favors again a twisted chair conformation.
    Citation
    J. Org. Chem. 2007, 72(10):3776-82
    URI
    http://hdl.handle.net/10033/13101
    DOI
    10.1021/jo070048w
    PubMed ID
    17428096
    Type
    Article
    Language
    en
    ISSN
    0022-3263
    ae974a485f413a2113503eed53cd6c53
    10.1021/jo070048w
    Scopus Count
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    publications of the research group microbial communication (KOM)

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