Chemoenzymatic preparation of dermatan sulfate oligosaccharides as arylsulfatase B and alpha-L-iduronidase substrates.
Dermatan sulfate was partially depolymerized with chondroitin ABC lyase to obtain an oligosaccharide mixture from which an unsaturated disulfated tetrasaccharide was purified and characterized using nuclear magnetic resonance spectroscopy and electrospray ionization mass spectrometry. Chemical removal of the unsaturated uronate residue with mercuric acetate, followed by de-4-O-sulfation with arylsulfatase B (N-acetylgalactosamine 4-sulfatase) and N- acetylhexosaminidase catalyzed removal of the 2-acetamido-2-deoxy-D-galactospyranosyl residue at the non-reducing end afforded a monosulfated disaccharide of the structure alpha-L-idopyranosyluronic acid (1-->3)-alpha,beta-D-2-acetamido-2-deoxy-4-O-sulfo galactopyranose. This monosulfated disaccharide serves as a substrate for mammalian alpha-L-iduronidase as demonstrated using fluorophore assisted carbohydrate electrophoresis.
Dasgupta
F
F
Biomarin Pharmaceutical, Novato, California, USA.
Masada
R I
RI
Starr
C M
CM
Kuberan
B
B
Yang
H O
HO
Linhardt
R J
RJ
D000818:Animals; D019765:Chondroitin ABC Lyase / Q000378:metabolism; D003871:Dermatan Sulfate / Q000096:biosynthesis* / Q000737:chemistry* / Q000378:metabolism; D004591:Electrophoresis, Polyacrylamide Gel; D005453:Fluorescence; D007068:Iduronidase / Q000378:metabolism*; D007413:Intestinal Mucosa; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D020051:N-Acetylgalactosamine-4-Sulfatase / Q000378:metabolism*; D009844:Oligosaccharides / Q000096:biosynthesis / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013552:Swine
D009844:Oligosaccharides; D003871:Dermatan Sulfate; D020051:N-Acetylgalactosamine-4-Sulfatase; D007068:Iduronidase; D019765:Chondroitin ABC Lyase