Acceptor hydroxyl group mapping for calf thymus α-(1 → 3)- galactosyltransferase and enzymatic synthesis of α-D-Galp-(1 → 3)-β-D- Galp-(1 → 4)-β D-GlcpNAc analogs

Keiko Sujino, Carles Malet, Ole Hindsgaul, Monica M. Palcic

Research output: Indexed journal article Articlepeer-review

28 Citations (Scopus)

Abstract

The epitope of the acceptor substrate for α-(1 → 3)- galactosyltransferase from calf thymus has been mapped by using a series of mono-deoxygenated and mono-O-alkylated Type II (β-D-Galp-(1 → 4)-β-D- GlcpNAc) disaccharides. The 4-OH group of the β-D-galactopyranosyl residue is a key polar group essential for glycosyl transfer, tolerating neither deoxygenation nor O-alkylation. Substitution at positions 6 and 6' by a variety of polar alkyl substituents was readily tolerated, allowing the preparative enzymatic synthesis of a series of trisaccharide derivatives carrying polar substituents on each of these hydroxyl groups. These new analogs are potential inhibitors of Clostridium difficile toxin A and of a human anti-α-Gal antibody.

Original languageEnglish
Pages (from-to)483-489
Number of pages7
JournalCarbohydrate Research
Volume305
Issue number3-4
DOIs
Publication statusPublished - Dec 1997
Externally publishedYes

Keywords

  • α-(1 → 3)-Galactosyltransferase
  • α-D-Galp-(1 → 3)-β-D-Galp-(1 → 4)- β-D-GlcpNAc, analogs

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