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'Structure Activity Relationship' in keywords Facet   section ZfN Section B:Volume 042  [X]
Facet   Publication Year 1987  [X]
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1Author    Harald Labischinski, Dieter Naumann, Gerhard Barnickel, Wolfgang Dreißig, Wojciech Gruszecki, Andreas Hofer, Hans BradaczekRequires cookie*
 Title    Comparison between the Molecular and Crystal Structures of a Benzylpenicillin Ester and its Corresponding Sulfoxide with Drastically Reduced Biological Activity  
 Abstract    A comparative X-ray structure determination was performed to elucidate possible conforma-tional differences between penicillins and penicillin sulfoxides. Penicillin-G-acetoxy-methylester and its Iß-oxide were used as model substances, because the only chemical difference between both compounds resides in the thiazolidine ring sulfur oxidation. On the basis of the X-ray data as well as of infrared measurements it is discussed that the drastically reduced biological activity of the penicillin-G-sulfoxide might be related to conformational differences in thiazolidine ring puckering or, even more simply, to the geometric position of the sulfoxide oxygen atom, both of which may hamper the proper reaction of the sulfoxide with its target enzyme(s). 
  Reference    Z. Naturforsch. 42b, 367—375 (1987); received June 30/0ctober 14 1986 
  Published    1987 
  Keywords    X-Ray, Penicillin G, Penicillin G Sulfoxide, Thiazolidine Ring Conformation, Structure Activity Relationships 
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 TEI-XML for    default:Reihe_B/42/ZNB-1987-42b-0367.pdf 
 Identifier    ZNB-1987-42b-0367 
 Volume    42