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Actinoidins A and A2: structure determination using 2D NMR methods.

S L Heald, L Mueller, P W Jeffs

    The Journal of Antibiotics
    |May 1, 1987
    PubMed
    Summary
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    This study used advanced NMR techniques to analyze the structure of glycopeptide antibiotics actinoidin A and A2. The key difference identified was the presence of L-rhamnose in actinoidin A2 instead of L-acosamine in actinoidin A.

    Area of Science:

    • Biochemistry
    • Organic Chemistry
    • Structural Biology

    Background:

    • Glycopeptide antibiotics are crucial therapeutic agents.
    • Understanding their precise structure is vital for drug development and efficacy.
    • Actinoidins A and A2 represent important classes of these antibiotics.

    Purpose of the Study:

    • To elucidate the complete structure of actinoidin A and the novel analog actinoidin A2.
    • To identify structural differences between actinoidin A and actinoidin A2.
    • To confirm the stereochemistry of chiral centers within the antibiotics.

    Main Methods:

    • Two-dimensional proton nuclear magnetic resonance (2D 1H NMR) spectroscopy was employed.
    • Techniques included correlation spectroscopy (COSY), double quantum coherence experiments (DQCE), homonuclear Hartmann-Hahn experiments (HOHAHA), and nuclear Overhauser spectroscopy (NOESY).

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  • These methods allowed for detailed structural analysis and assignment of atomic connectivities and spatial proximities.

    • Main Results:

    • The chlorine atom in actinoidin A was located at the A3 position.
    • The attachment sites of four carbohydrate substituents in actinoidin A were determined.
    • Actinoidin A2 was identified as a novel analog, differing from actinoidin A by the presence of L-rhamnose instead of L-acosamine.

    Conclusions:

    • The structural analysis confirmed the molecular architecture of actinoidins A and A2.
    • The study successfully resolved the stereochemistry of most chiral centers, with the exception of the N-terminal amino acid's alpha-carbon.
    • This detailed structural information provides a foundation for further research into the function and synthesis of these glycopeptide antibiotics.