Ring Flip of Carbohydrates: Functions and Applications
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- Yuasa Hideya
- Department of Life Science, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology
Bibliographic Information
- Other Title
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- 糖の環フリップ:機能と応用
- トウ ノ カン フリップ キノウ ト オウヨウ ガン エイブン
- Functions and Applications
- 機能と応用
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Abstract
The mechanochemical studies of carbohydrate ring flipping by both top-down and bottom-up approaches are surveyed. In the top-down approaches, the traction studies of polysaccharides by atomic force microscopy (AFM) disclosed their interesting behavior: they become abruptly flexible at certain pulling forces due to the synchronous ring flips of the monosaccharide units. This abrupt flexibility confers a shockabsorbing mechanism on glycoproteins and glyco-coated cells. Regarding the bottom-up approach, we succeeded in controlling the ring flip of carbohydrates to find that a 2, 4-diaminoxylose derivative (hinge sugar) easily undergoes the ring flip by chelation to a metal ion at the amino groups. The metal-ion-induced bending of the hinge sugar was even more efficient when it was incorporated in a trisaccharide, probably due to the interaction between the reducing and non-reducing terminus sugars. For application, we invented a hinge-sugar-based metal ion sensor, in which a chelationdriven and pliers-like motion of the dipyrenylmethyl hinge sugar causes stacking of two pyrene groups, giving rise to excimer fluorescence. Hinge sugar was also applicable to the tether in a [2+2] cycloaddition reaction. These studies emphasize a new aspect of carbohydrates as motional components in biology and material science.
Journal
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- Trends in Glycoscience and Glycotechnology
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Trends in Glycoscience and Glycotechnology 18 (104), 353-370, 2006
FCCA(Forum: Carbohydrates Coming of Age)
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Keywords
Details 詳細情報について
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- CRID
- 1390001204368951296
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- NII Article ID
- 10018515985
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- NII Book ID
- AA10995236
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- ISSN
- 18832113
- 09157352
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- NDL BIB ID
- 8682765
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- Text Lang
- ja
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed