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Synthesis and photochromic properties of configurationally varied azobenzene glycosides.

ABSTRACT: Spatial orientation of carbohydrates is a meaningful parameter in carbohydrate recognition processes. To vary orientation of sugars with temporal and spatial resolution, photosensitive glycoconjugates with favorable photochromic properties appear to be opportune. Here, a series of azobenzene glycosides were synthesized, employing glycoside synthesis and Mills reaction, to allow "switching" of carbohydrate orientation by reversible E/Z isomerization of the azobenzene N=N double bond. Their photochromic properties were tested and effects of azobenzene substitution as well as the effect of anomeric configuration and the orientation of the sugars 2-hydroxy group were evaluated.

SUBMITTER: Chandrasekaran V

PROVIDER: S-EPMC4101725 | biostudies-literature | 2014 Jun

REPOSITORIES: biostudies-literature

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Synthesis and photochromic properties of configurationally varied azobenzene glycosides.

Chandrasekaran Vijayanand V Johannes Eugen E Kobarg Hauke H Sönnichsen Frank D FD Lindhorst Thisbe K TK

ChemistryOpen 20140618 3

Spatial orientation of carbohydrates is a meaningful parameter in carbohydrate recognition processes. To vary orientation of sugars with temporal and spatial resolution, photosensitive glycoconjugates with favorable photochromic properties appear to be opportune. Here, a series of azobenzene glycosides were synthesized, employing glycoside synthesis and Mills reaction, to allow "switching" of carbohydrate orientation by reversible E/Z isomerization of the azobenzene N=N double bond. Their photoc ...[more]

PMID: 25050228

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