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Improved synthesis of UDP-2-(2-ketopropyl)galactose and a first synthesis of UDP-2-(2-ketopropyl)glucose for the site-specific linking of biomolecules via modified glycan residues using glycosyltransferases

  1. Author:
    Dulcey, A. E.
    Qasba, P. K.
    Lamb, J.
    Griffiths, G. L.

  2. Author Address

    [Dulcey, AE; Lamb, J; Griffiths, GL] NHLBI, Imaging Probe Dev Ctr, NIH, Rockville, MD 20850 USA [Qasba, PK] NCI, Struct Glycobiol Sect, Nanobiol Program, Ctr Canc Res, Frederick, MD 21702 USA;Dulcey, AE (reprint author), NHLBI, Imaging Probe Dev Ctr, NIH, 9800 Med Ctr Dr, Rockville, MD 20850 USA;dulceyan@mail.nih.gov
    1. Year: 2011
    2. Date: Mar
  2. Journal: Tetrahedron
    1. 67
    2. 11
    3. Pages: 2013-2017
  4. Type of Article: Article
  5. ISSN: 0040-4020
  1. Abstract:

    The potential of wild-type and mutant glycosyltransferases to produce glycoconjugates carrying sugar moieties with chemical handles has made it possible to conjugate biomelecules with orthogonal reacting groups at specific sites. The synthesis of UDP-2-(2-ketopropyl)galactose has been previously carried out, albeit with difficulty and low efficiency. A modified approach has been developed for the synthesis of UDP-2-(2-ketopropyl)glucose and UDP-2-(2-ketopropyl)galactose, allowing better access to the desired test compounds, the UDP-2-(2-ketopropyl)glucose and UDP-2-(2-ketopropyl)galactose analogs were synthesized in eight steps and 4.8% and 5.3% overall yield, respectively, an improvement over the first generation synthesis involving eight steps and an overall yield of 0.7%. Published by Elsevier Ltd.

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External Sources

  1. View Full Text
  2. DOI: 10.1016/j.tet.2011.01.081
  3. View record in Web of Science®
  4. WOS: 000293037300002

Library Notes

  1. Fiscal Year: FY2010-2011
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