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Related Experiment Videos

Ring-chain tautomerism in solid-phase erythromycin A: evidence by solid-state NMR.

Robbie J Iuliucci1, Jacalyn Clawson, Jain Zhi Hu

  • 1Department of Chemistry, Washington and Jefferson College, Washington, PA 15301, USA. riuliucci@washjeff.edu

Solid State Nuclear Magnetic Resonance
|July 10, 2003
PubMed
Summary

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Solid-state NMR reveals erythromycin A forms a cyclic hemiketal in its solid phase. This study provides the first measurement of hemiketal 13C chemical shift tensor values, distinct from anomeric carbons.

Area of Science:

  • Solid-state chemistry
  • Organic chemistry
  • Spectroscopy

Background:

  • Erythromycin A is a vital antibiotic with complex solid-state properties.
  • Understanding its solid-phase behavior is crucial for formulation and stability.
  • Previous studies have not fully elucidated the solid-state structural transformations of erythromycin A.

Purpose of the Study:

  • To investigate the structural changes of erythromycin A in the solid phase using solid-state Nuclear Magnetic Resonance (NMR).
  • To identify the nature of a newly observed carbon resonance under specific conditions.
  • To characterize the chemical shift tensor of the identified functional group.

Main Methods:

  • Solid-state 13C magic-angle spinning (MAS) NMR spectroscopy.
  • Chemical shift modeling using Density Functional Theory (DFT) with the B3LYP/D95** method.

Related Experiment Videos

  • Dipolar-dephasing spectral editing techniques.

    • Main Results:

    • Detailed spectral assignment of 35 visible 13C resonances for solid-phase erythromycin A dihydrate.
    • Observation of a new resonance at 110.8 ppm upon heating or desiccation.
    • Identification of this new resonance as a hemiketal carbon using dipolar-dephasing, ruling out an anomeric carbon conformational change.
    • Reporting of the first measured 13C chemical shift tensor principal values for a hemiketal.

    Conclusions:

    • Solid-state NMR definitively proves the formation of a cyclic hemiketal in erythromycin A.
    • The measured hemiketal 13C chemical shift tensor components are unique and differ from reported anomeric carbon values.
    • This finding offers new insights into the solid-state chemistry of erythromycin A.