Communication: Synthesis of a Library of β-GlcNAc Glycosides to Screen for Efficient in Vivo Glycosyltransferase Acceptors
Titel:
Communication: Synthesis of a Library of β-GlcNAc Glycosides to Screen for Efficient in Vivo Glycosyltransferase Acceptors
Auteur:
Ding, Yili Miura, Yoshiaki Etchison, James R. Freeze, Hudson H. Hindsgaul, Ole
Verschenen in:
Journal of carbohydrate chemistry
Paginering:
Jaargang 18 (1999) nr. 4 pagina's 471-475
Jaar:
1999
Inhoud:
Artificial glycosides are used to prime the biosynthesis of glycosaminoglycan chains and those typical of N- and O-linked oligosaccharides, e.g., N-acetyllactosamine repeats.1-8 Several studies have shown that the aglycon influences the amount and type of products assembled on such glycosides.2-6 The amount of product made depends on two factors. The first is the ability of the glycoside to penetrate the plasma membrane and the Golgi membrane where the glycosyltransferases are located. The second is the structure of the aglycon since it can influence the addition of the first monosaccharide as well as extension with additional residues. In some instances, the aglycon is thought to mimic a portion of an underlying polypeptide chain.2-4,6 The choice of aglycons is important, but there are no guidelines to direct the choice since many factors such as their stability to glycosidases, membrane-permeability, cellular toxicity or limitation of specificity and affinity can all be important. In the absence of such guidelines, we streamlined the process of aglycon evaluation and report here an efficient strategy to synthesize GlcNAcβ-R libraries with various aglycons.