Tandem exploitation of Helix pomatia glycosyltransferases: facile syntheses of H-antigen-bearing oligosaccharides.
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Tandem exploitation of Helix pomatia glycosyltransferases: facile syntheses of H-antigen-bearing oligosaccharides. / Bretting, Hagen; Buck, Friedrich; Jacobs, Günter; Meinke, Sebastian; Scheppokat, Angela M; Thiem, Joachim.
In: CHEM-EUR J, Vol. 13, No. 25, 25, 2007, p. 7144-7152.Research output: SCORING: Contribution to journal › SCORING: Journal article › Research › peer-review
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T1 - Tandem exploitation of Helix pomatia glycosyltransferases: facile syntheses of H-antigen-bearing oligosaccharides.
AU - Bretting, Hagen
AU - Buck, Friedrich
AU - Jacobs, Günter
AU - Meinke, Sebastian
AU - Scheppokat, Angela M
AU - Thiem, Joachim
PY - 2007
Y1 - 2007
N2 - Snails from the family Helicidae produce in their albumen glands a highly branched galactan, which consists almost exclusively of D- and L-galactose. The D-Gal residues are glycosydically beta(1-->6)- or beta(1-->3)-linked, whereas the L-Gal moieties are attached alpha(1-->2). Up until the present time, two beta(1-->6)-D-galactosyl transferases and one alpha(1-->2)-L-galactosyl transferase have been identified in a membrane preparation of these glands. These were used to synthesise various oligosaccharides by successive addition of the NDP-activated (NDP=nucleoside-5'-diphosphate) D-Gal or L-Fuc moieties, up to a heptasaccharide by starting from the disaccharide D-Gal-beta(1-->3)-D-Gal-beta(1-->OMe. Even larger oligosaccharides up to a tridecasaccharide were obtained by starting with the hexasaccharide D-Gal-[beta(1-->3)-D-Gal]4-beta(1-->4)-D-Glc as an acceptor substrate. This tandem exploitation process has high potential for the easy introduction of D-Gal and L-Fuc residues into a great variety of oligosaccharides, which can be used in ligand/acceptor studies.
AB - Snails from the family Helicidae produce in their albumen glands a highly branched galactan, which consists almost exclusively of D- and L-galactose. The D-Gal residues are glycosydically beta(1-->6)- or beta(1-->3)-linked, whereas the L-Gal moieties are attached alpha(1-->2). Up until the present time, two beta(1-->6)-D-galactosyl transferases and one alpha(1-->2)-L-galactosyl transferase have been identified in a membrane preparation of these glands. These were used to synthesise various oligosaccharides by successive addition of the NDP-activated (NDP=nucleoside-5'-diphosphate) D-Gal or L-Fuc moieties, up to a heptasaccharide by starting from the disaccharide D-Gal-beta(1-->3)-D-Gal-beta(1-->OMe. Even larger oligosaccharides up to a tridecasaccharide were obtained by starting with the hexasaccharide D-Gal-[beta(1-->3)-D-Gal]4-beta(1-->4)-D-Glc as an acceptor substrate. This tandem exploitation process has high potential for the easy introduction of D-Gal and L-Fuc residues into a great variety of oligosaccharides, which can be used in ligand/acceptor studies.
M3 - SCORING: Zeitschriftenaufsatz
VL - 13
SP - 7144
EP - 7152
JO - CHEM-EUR J
JF - CHEM-EUR J
SN - 0947-6539
IS - 25
M1 - 25
ER -