The importance of correct tautomeric structures for biological molecules

Poul Erik Hansen, John Mortensen, Fadhil S. Kamounah

Publikation: Bidrag til tidsskriftTidsskriftartikelpeer review

Abstract

The structures of usnic acid and tetracycline are determined using deuterium isotope effects on 13C chemical shifts in a water environment. In case of usnic acid this is achieved by synthesizing a more water soluble usnic acid with a PEG linker. In the usnic acid case an enolic b-triketone (C-1, C-14 and C-3) tautomeric equilibrium is at hand below pH 5. At pH 7.4 it exists as a mono anion. In case of tetracycline equilibrium between a zwitter ion and a neutral form is found together with an amide functional group and a hydrogen bonded enolic b-diketone system shifted strongly towards one tautomer.
OriginalsprogEngelsk
TidsskriftJSM chemistry
Vol/bind3
Udgave nummer1
Sider (fra-til)1014-18
Antal sider5
StatusUdgivet - 14 jan. 2015

Emneord

  • tautomeri
  • structure-function relationship
  • NMR
  • isotoope effects
  • usnic acid
  • tetracycline

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