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

2.50
Hdl Handle:
http://hdl.handle.net/10033/13101
Title:
Identification, synthesis, and conformation of tri- and tetrathiacycloalkanes from marine bacteria.
Authors:
Sobik, Paul; Grunenberg, Jörg; Böröczky, Katalin; Laatsch, Hartmut; Wagner-Döbler, Irene; Schulz, Stefan
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
Issue Date:
11-May-2007
URI:
http://hdl.handle.net/10033/13101
DOI:
10.1021/jo070048w
PubMed ID:
17428096
Type:
Article
Language:
en
ISSN:
0022-3263
Appears in Collections:
collections of the research group microbial communication (KOM)

Full metadata record

DC FieldValue Language
dc.contributor.authorSobik, Paul-
dc.contributor.authorGrunenberg, Jörg-
dc.contributor.authorBöröczky, Katalin-
dc.contributor.authorLaatsch, Hartmut-
dc.contributor.authorWagner-Döbler, Irene-
dc.contributor.authorSchulz, Stefan-
dc.date.accessioned2007-08-03T14:06:02Z-
dc.date.available2007-08-03T14:06:02Z-
dc.date.issued2007-05-11-
dc.identifier.citationJ. Org. Chem. 2007, 72(10):3776-82en
dc.identifier.issn0022-3263-
dc.identifier.pmid17428096-
dc.identifier.doi10.1021/jo070048w-
dc.identifier.urihttp://hdl.handle.net/10033/13101-
dc.description.abstractSeven 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.en
dc.format.extent558113 bytes-
dc.format.mimetypeapplication/pdf-
dc.language.isoenen
dc.titleIdentification, synthesis, and conformation of tri- and tetrathiacycloalkanes from marine bacteria.en
dc.typeArticleen
dc.format.digYES-

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