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Degradation of Target Oligosaccharides by Anthraquinone–Lectin Hybrids with Light Switching
Author(s) -
Imai Yukari,
Hirono Shingo,
Matsuba Haruka,
Suzuki Tomohiro,
Kobayashi Yuka,
Kawagishi Hirokazu,
Takahashi Daisuke,
Toshima Kazunobu
Publication year - 2012
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201100586
Subject(s) - anthraquinone , glycosidic bond , chemistry , concanavalin a , lectin , residue (chemistry) , oligosaccharide , biochemistry , sugar , organic chemistry , in vitro , enzyme
Abstract Anthraquinone–lectin hybrids were effectively synthesized using water‐soluble anthraquinone derivative 11 with concanavalin A (ConA) and hygrophorus russula lectin (HRL) to give anthraquinone–ConA ( 16 ) and anthraquinone–HRL ( 17 ) hybrids, respectively. These anthraquinone–lectin hybrids effectively and selectively degraded oligosaccharides containing a mannose residue as a non‐reducing terminal sugar, which has affinity for ConA and HRL, under photo‐irradiation with long‐wavelength UV light without additives and under neutral conditions. In addition , anthraquinone–HRL ( 17 ) selectively photo‐degraded only Man(α1,6)Man, which has a high affinity for HRL, among several mannosides by recognition of both the type and glycosidic linkage profile of the sugar in an oligosaccharide.