Bausteine von Oligosacchariden, CII. Synthese von modifizierten Derivaten der 2‐Acetamido‐2‐desoxy‐D‐galactose zur Untersuchung der Substratspezifität der Core‐1‐β3‐Gal‐Transferase und der Core‐3‐β3‐GlcNAc‐Transferase der Biosynthese von O‐Glycoproteinen

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Abstract
Building Units of Oligosaccharides, CII. – Synthesis of Modified Derivatives of 2‐Acetamido‐2‐deoxy‐D‐galactose for the Examination of Substrate Specificities of Core 1‐β3‐Gal‐Transferase and Core 3‐β3‐GlcNAc‐Transferase Involved in the Biosynthesis of O‐GlycoproteinsThe 2‐, 3‐, 4‐, and 6‐deoxy derivatives of benzyl 2‐acetamido‐2‐deoxy‐α‐D‐galactopyranoside (7) have been synthesized to test substrate specificities of glycosyltransferases involved in the biosynthesis of O‐glycoproteins. The core 1‐β3‐Gal‐transferase dose not require the 6‐hydroxyl group for activity in contrast to the glycosylation reaction of the core 3‐β3‐GlcNAc‐transferase which requires the 6‐hydroxyl group. Compounds with reactive groups substituting the 6‐hydroxyl group such as the diazirine 45 could be suitable for photolabeling of the former enzyme. A column for affinity chromatography with the 6‐deoxy derivative as the ligand could be useful to separate the two enzymes during purification.

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