Degradation of target oligosaccharides by anthraquinone-lectin hybrids with light switching

Yukari Imai; Shingo Hirono; Haruka Matsuba; Tomohiro Suzuki; Yuka Kobayashi; Hirokazu Kawagishi; Daisuke Takahashi; Kazunobu Toshima

doi:10.1002/asia.201100586

Degradation of target oligosaccharides by anthraquinone-lectin hybrids with light switching

Chem Asian J. 2012 Jan 2;7(1):97-104. doi: 10.1002/asia.201100586. Epub 2011 Oct 13.

Authors

Yukari Imai¹, Shingo Hirono, Haruka Matsuba, Tomohiro Suzuki, Yuka Kobayashi, Hirokazu Kawagishi, Daisuke Takahashi, Kazunobu Toshima

Affiliation

¹ Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Kohoku-ku, Yokohama, Japan.

PMID: 21997955
DOI: 10.1002/asia.201100586

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anthraquinones / chemistry*
Lectins / chemistry*
Molecular Structure
Oligosaccharides / chemistry*
Solubility
Ultraviolet Rays*
Water / chemistry

Substances

Anthraquinones
Lectins
Oligosaccharides
Water