Synthesis of linear-B saccharopeptides via enzymatic galactosylation of non-natural glucosamide acceptors.
A series of D- and L-glycopyranuronic acids are coupled to glucosamines to give saccharopeptides. These 'disaccharides', in which the acetyl moiety of the natural N-acetyl-glucosamine is replaced by various sugar acids, turned out to be surprisingly good substrates for beta(1-4)-galactosyl-transferase and alpha(1-3)-galactosyl-transferase. The enzymes transfer successively two galactose units from the donor UDP-galactose onto these acceptor substrates, despite the far reaching alterations, regio- and stereospecifically in the expected manner to give linear-B saccharopeptides.
Schwardt
O
O
Novartis Pharma AG, Postfach, CH-4002 Basel, Switzerland. oliver.schwardt@unibas.ch
Baisch
G
G
Ohrlein
R
R
D000577:Amides / Q000737:chemistry*; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D005690:Galactose / Q000737:chemistry*; D005700:Galactosyltransferases / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009237:N-Acetyllactosamine Synthase / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry
D000577:Amides; D002241:Carbohydrates; D010455:Peptides; D005700:Galactosyltransferases; C047006:N-acetyllactosaminide alpha-1,3-galactosyltransferase; D009237:N-Acetyllactosamine Synthase; D005690:Galactose