New sugar chain null for sugar transferring enzyme official approval

摘要

PURPOSE:To provide the subject novel sugar chain capable of detecting a sugar transferase acting as a cellular function-manifesting factor, etc., with ultra-violet rays in high sensitivity by introducing an ultra-violet ray-coloring m-nitrobenzyl group into the spacer part of the sugar chain. CONSTITUTION:A compound of formula I (Bn is benzyl) is made to react with two equivalents of a compound of formula II (Ac is acetyl; Phth is phthaloyl). The reactional product is subjected to a phthaloyl group-removing reaction, an acetylation reaction, a catalytic reduction reaction, a deacetylation reaction, a deallylation reaction, a debenzylation reaction, an acetylation reaction and further a hydrazine acetate treatment. The reactional product is subjected to a deacetylation reaction only at the 1-position and reacted with a formula Cl3CCN to produce a compound of formula III [R1 is C(=NH)CCl3; R2, R4, R5 are Ac; R3 is H], which is subjected to a glycosylation reaction with a compound of formula IV, and further to debenzylation reaction, a deacetylation reaction, an ester exchange reaction, and an ester exchange reaction in m- nitrobenzyl alcohol to produce the objective sugar chain of formula V (R1 is m-nitrobenzyl; R3 is N-acetyl-D-glucosamine).