Sugar chain containing 4-position halogenated galactose and application thereof

A method for producing a second acceptor compound having at an end thereof a 4-position halogenated galactose residue comprising:

• contacting a first acceptor compound for a 4-position halogenated galactose residue, which is a monosaccharide, an oligosaccharide, an oligosaccharide bound to a carrier, or an immobilized saccharide bonded to a carrier, optionally via a spacer, with a glycosyltransferase and a sugar donor that is a halogenated galactose sugar nucleotide represented by formula (II):
• wherein each of R1 to R3 represents a hydroxyl group, an acetyl group, a halogen atom, or a hydrogen atom;
• X represents a halogen atom;
• and M+ represents a hydrogen ion or a metal ion;
• wherein said glycosyltransferase is selected from the group consisting of a β1,4-galactosyltransferase, a β1,3-galactosyltransferase, and an α-1,3-galactosyltransferase;
• or another galactosyltransferase that transfers a 4-deoxy-4-halogeno-galactosyl group to said sugar donor.

A method for producing a 4-position halogenated galactose sugar nucleotide (II), comprising:

• phosphorylating a compound represented by formula (III) by contacting it with phosphate ion in the presence of a bacterial galactokinase, thus forming a compound represented by formula (IV), and
• contacting the compound represented by formula (IV) and a uridine sugar nucleotide with a bacterial hexose-1-phosphate uridylyltransferase, thus synthesizing a compound represented by formula (II);
• wherein formulas (II), (III) and (IV) are:
• wherein each of R1 to R3 represents a hydroxyl group, an acetyl group, a halogen atom, or a hydrogen atom;
• R4 represents a phosphate residue or a salt thereof;
• X represents a halogen atom;
• and M+ represents a hydrogen ion or a metal ion.