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Synthesis and Structure of Vitamin B12-Derivatives with a Modified Ribose-Unit

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Summary.

The acylation at the 5′-OH group of the ribose-unit of vitamin B12 (cyanocobalamin) or of aquocobalamin with two conventional reagents gave mono-acylated B12-derivatives with good to very high selectivity. The site of the modification was deduced from spectral data of the products and was further supported by the crystal structure data of three such modified B12-derivatives. These three B12-derivatives were found to crystallize in the space group P212121, irrespective of the nature of the appendage. Acylation at 5′-OH has been used to protect (or block) this group in the context of functionalization of 2′-OH or elsewhere in the B12-molecule. Attachment of the bifunctional succinyl-unit has allowed the preparation of further modified derivatives of vitamin B12 and binding of B12-derivatives to biological carriers and other macromolecules. In aqueous solution, 5′-acylcobalamins turned out to be rather susceptible to hydrolytic loss of the acyl-functionality.

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Authors and Affiliations

  1. Institute of Organic Chemistry and Centre of Molecular Biosciences, University of Innsbruck, Innsbruck, Austria

    Renate B. Hannak, Sigrid Gschösser & Bernhard Kräutler

  2. Nestec S.A., Orbe, Switzerland

    Renate B. Hannak

  3. Institute of General, Inorganic and Theoretical Chemistry, University of Innsbruck, Innsbruck, Austria

    Klaus Wurst

Authors
  1. Renate B. Hannak
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  2. Sigrid Gschösser
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  3. Klaus Wurst
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  4. Bernhard Kräutler
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Correspondence to Bernhard Kräutler.

Additional information

Bernhard Kräutler: In memoriam Prof. Karl Schlögl

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Hannak, R., Gschösser, S., Wurst, K. et al. Synthesis and Structure of Vitamin B12-Derivatives with a Modified Ribose-Unit. Monatsh. Chem. 138, 899–907 (2007). https://doi.org/10.1007/s00706-007-0752-9

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  • DOI: https://doi.org/10.1007/s00706-007-0752-9

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