Oligosaccharide Sensing in Aqueous Media Using Porphyrin–Curdlan Conjugates: An Allosteric Signal-Amplification System | Zendy

Mayuko Sasaki | Zendy; Yuma Ryoson | Zendy; Munenori Numata | Zendy; Gaku Fukuhara | Zendy

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Oligosaccharide Sensing in Aqueous Media Using Porphyrin–Curdlan Conjugates: An Allosteric Signal-Amplification System

Author(s) -

Mayuko Sasaki,

Yuma Ryoson,

Munenori Numata,

Gaku Fukuhara

Publication year - 2019

Publication title -

the journal of organic chemistry

Language(s) - Uncategorized

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.9b00040

Subject(s) - chemistry , curdlan , porphyrin , acarbose , aqueous solution , circular dichroism , conjugate , oligosaccharide , stereochemistry , cooperativity , stacking , photochemistry , organic chemistry , biochemistry , polysaccharide , mathematical analysis , mathematics , enzyme

A series of porphyrin-curdlan conjugates 1-5 of varying degree of substitution (DS) were synthesized to examine their morphological features, chiroptical properties, and oligosaccharide sensing in aqueous media, particularly for tetrasaccharide acarbose, which is a drug to treat type-2 diabetes. The random coil state of compounds 1-5 in DMSO becomes the globule curdlan-saccharide coaggregate upon interaction of acarbose in aqueous DMSO solution to induce various circular dichroism (CD) responses. The high cooperativity and positive homotropic allosterism were observed in the acarbose recognition, enabling the allosteric signal-amplification sensing, for which the DS, stacking character, and microenvironmental polarity changes of the tethered porphyrin reporters are likely to be responsible.

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