Process for producing hydrazinomonosaccharide derivatives and use thereof

A method for identifying a monosaccharide at a reducing end of a saccharide having the reducing end and/or for determining a position of binding of a monosaccharide at a reducing end to a neighboring monosaccharide, the method comprising at least:

• (a) reacting a saccharide having a reducing end with a hydrazine of formula (I) to produce a hydrazone:
• NH2—NR1(R2) (I)
• wherein R1 is a group other than hydrogen that has a detectable label and/or an immobilization support as its portion or can bind to a detectable label and/or an immobilization support;
• the bond between R1 and N is a bond that is cleavable by a reaction that can cleave a glycosidic linkage;
• and R2 is hydrogen or an alkyl group containing 1-8 carbon atoms;
• (b) reducing the hydrazone obtained in step (a) to a hydrazino derivative;
• (c) cleaving the hydrazino derivative obtained in step (b) by the reaction that can cleave a glycosidic linkage to obtain a hydrazino monosaccharide derivative;
• (d) completely acetylating the hydrazino monosaccharide derivative obtained in step (c);
• and
• (e) identifying the completely acetylated hydrazino monosaccharide derivative obtained in step (d).

A method for labeling a saccharide having a reducing end, the method comprising at least:

• (a) reacting a saccharide having a reducing end with a hydrazine of formula (I) to produce a hydrazone:
• NH2—NR1(R2) (I)
• wherein R1 is a group other than hydrogen that has a detectable label and/or an immobilization support as its portion or can bind to a detectable label and/or an immobilization support;
• the bond between R1 and N is a bond that is cleavable by a chemical reaction that can cleave a glycosidic linkage;
• and R2 is hydrogen or an alkyl group of 1-8 carbon atom(s);
• (b) reducing the hydrazone obtained in step (a) to a hydrazino derivative;
• and
• (c) N-acetylating the hydrazino derivative obtained in step (b).

A saccharide of formula (III):

• R4—N(Ac)—NHR1 (III)
• wherein Ac is an acetyl group;
• R1 is a group other than hydrogen that has a detectable label and/or an immobilization support as its portion or can bind to a detectable label and/or an immobilization support;
• the bond between R1 and N is a bond that is cleavable by a chemical reaction that can cleave a glycosidic linkage;
• R4 is a group that may have a glycosidic linkage with a saccharide and from which one hydrogen atom linked to the C-1 position of a 1-deoxy aldose or one hydrogen atom linked to the C-2 carbon of a 2-deoxy ketose is removed, excluding a case where R1 is an acetyl group, and R4 is a group that does not have a glycosidic linkage with a saccharide and from which one hydrogen atom linked to the C-1 position of a 1deoxy aldose or one hydrogen atom linked to the C-2 carbon of a 2-deoxy ketose is removed.