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Efficient chemoenzymatic synthesis of o-linked sialyl oligosaccharides

Academic Article
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Overview

authors

  • Blixt, O.
  • Allin, K.
  • Pereira, L.
  • Datta, A.
  • Paulson, James

publication date

  • May 2002

journal

  • Journal of the American Chemical Society  Journal

abstract

  • The tumor associated Tn (GalNAcalpha(1-1)-Thr/Ser)- and T (Galbeta(1-3)-GalNAcalpha(1-1)Thr/Ser)-antigens and their sialylated derivatives are present on the surface of many cancer cells. Preparative synthesis of these sialylated T- and Tn-structures has been achieved mainly from a chemical synthetic approach due to the lack of the required glycosyltransferases. We demonstrate a flexible and efficient chemoenzymatic approach for using recombinant sialyltransferases including a chicken GalNAcalpha2,6-sialyltransferase (chST6GalNAc I) and a porcine Galbeta(1-3)GalNAcalpha-2,3-sialyltransferase (pST3Gal I). Using these enzymes, the common O-linked sialosides Neu5Acalpha(2-6)GalNAcalpha(1-1)Thr, Galbeta(1-3)[Neu5Acalpha(2-6)]GalNAcalpha(1-1)Thr, Neu5Acalpha(2-3)Galbeta(1-3)GalNAcalpha(1-1)Thr, and Neu5Acalpha(2-3)Galbeta(1-3)[Neu5Acalpha(2-6)]GalNAcalpha(1-1)Thr were readily prepared at preparative scale. The chST6GalNAc I was found to require at least one amino acid (Thr/Ser) for optimal activity, and is thus an ideal catalyst for synthesis of synthetic glycopeptides and glycoconjugates with O-linked glycans.

subject areas

  • Animals
  • Antigens, Tumor-Associated, Carbohydrate
  • Carbohydrate Sequence
  • Chickens
  • Molecular Sequence Data
  • Mucins
  • Recombinant Proteins
  • Sialyltransferases
  • Substrate Specificity
  • Swine
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja017881+

PubMed ID

  • 12010048
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Additional Document Info

start page

  • 5739

end page

  • 5746

volume

  • 124

issue

  • 20

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