Literature DB >> 11982364

Chromophore formation in resorcinarene solutions and the visual detection of mono- and oligosaccharides.

Ming He1, Rolanda J Johnson, Jorge O Escobedo, Patricia A Beck, Kyu Kwang Kim, Nadia N St Luce, Claude J Davis, Patrick T Lewis, Frank R Fronczek, Bruce J Melancon, Anthony A Mrse, W Dale Treleaven, Robert M Strongin.   

Abstract

The colorimetric properties of resorcinarene solutions had not been investigated since Baeyer's initial synthesis. We recently reported that solutions containing resorcinarene macrocycles develop color upon heating or standing. In the presence of saccharides, these solutions exhibit significant color changes which are easily seen. We herein present strong evidence that the solution color is due to macrocycle ring opening and oxidation. The optical responses to saccharides are due to complexation of the sugar with the acyclic chromophores. We apply these mechanistic insights toward the challenging problem of the visual detection of neutral oligosaccharides by simple chromogens. In addition, we also report the first single-crystal X-ray crystal structure determination of a rarely observed "diamond" resorcinarene stereoisomer.

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Year:  2002        PMID: 11982364      PMCID: PMC3386614          DOI: 10.1021/ja017713h

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  11 in total

Review 1.  The impact of glycobiology on medicine.

Authors:  J Axford
Journal:  Trends Immunol       Date:  2001-05       Impact factor: 16.687

2.  Visual sensing of saccharides promoted by resorcinol condensation products

Authors: 
Journal:  Org Lett       Date:  2000-03-09       Impact factor: 6.005

3.  Simple and rapid visual sensing of saccharides.

Authors:  C J Davis; P T Lewis; M E McCarroll; M W Read; R Cueto; R M Strongin
Journal:  Org Lett       Date:  1999-07-29       Impact factor: 6.005

4.  Carceplexes and Hemicarceplexes.

Authors:  Ayub Jasat; John C. Sherman
Journal:  Chem Rev       Date:  1999-04-14       Impact factor: 60.622

5.  SHELXL: high-resolution refinement.

Authors:  G M Sheldrick; T R Schneider
Journal:  Methods Enzymol       Date:  1997       Impact factor: 1.600

Review 6.  HPLC of oligosaccharides in glycobiology.

Authors:  J M Lo-Guidice; M Lhermitte
Journal:  Biomed Chromatogr       Date:  1996 Nov-Dec       Impact factor: 1.902

7.  Space-group revision for 4-formylphenylboronic acid.

Authors:  F R Fronczek; N N St Luce; R M Strongin
Journal:  Acta Crystallogr C       Date:  2001-12-06       Impact factor: 1.172

8.  New color chemosensors for monosaccharides based on azo dyes.

Authors:  N DiCesare; J R Lakowicz
Journal:  Org Lett       Date:  2001-11-29       Impact factor: 6.005

Review 9.  Chemical glycobiology.

Authors:  C R Bertozzi; L L Kiessling
Journal:  Science       Date:  2001-03-23       Impact factor: 47.728

10.  Solid-state supramolecular structures of resorcinol-arylboronic acid compounds.

Authors:  C J Davis; P T Lewis; D R Billodeaux; F R Fronczek; J O Escobedo; R M Strongin
Journal:  Org Lett       Date:  2001-08-09       Impact factor: 6.005

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  10 in total

1.  Postcolumn HPLC detection of mono- and oligosaccharides with a chemosensor.

Authors:  Kyu Kwang Kim; Jorge O Escobedo; Nadia N St Luce; Oleksandr Rusin; Douglas Wong; Robert M Strongin
Journal:  Org Lett       Date:  2003-12-25       Impact factor: 6.005

2.  A convenient preparation of xanthene dyes.

Authors:  Youjun Yang; Jorge O Escobedo; Alexander Wong; Corin M Schowalter; Michael C Touchy; Lijuan Jiao; William E Crowe; Frank R Fronczek; Robert M Strongin
Journal:  J Org Chem       Date:  2005-08-19       Impact factor: 4.354

3.  Stereochemical and regiochemical trends in the selective detection of saccharides.

Authors:  Shan Jiang; Jorge O Escobedo; Kyu Kwang Kim; Onur Alptürk; George K Samoei; Sayo O Fakayode; Isiah M Warner; Oleksandr Rusin; Robert M Strongin
Journal:  J Am Chem Soc       Date:  2006-09-20       Impact factor: 15.419

4.  Macrocycle-derived functional xanthenes and progress towards concurrent detection of glucose and fructose.

Authors:  Oleksandr Rusin; Onur Alpturk; Ming He; Jorge O Escobedo; Shan Jiang; Fareed Dawan; Kun Lian; Matthew E McCarroll; Isiah M Warner; Robert M Strongin
Journal:  J Fluoresc       Date:  2004-09       Impact factor: 2.217

5.  Optimising the synthesis and red-green-blue emission of a simple organic dye.

Authors:  Martha Sibrian-Vazquez; Robert Strongin
Journal:  Supramol Chem       Date:  2010-12-14       Impact factor: 1.688

Review 6.  Differential sensing of sugars by colorimetric arrays.

Authors:  Christopher J Musto; Kenneth S Suslick
Journal:  Curr Opin Chem Biol       Date:  2010-08-05       Impact factor: 8.822

7.  Chiral recognition of amino acids by use of a fluorescent resorcinarene.

Authors:  Gerald I Richard; Hadi M Marwani; Shan Jiang; Sayo O Fakayode; Mark Lowry; Robert M Strongin; Isiah M Warner
Journal:  Appl Spectrosc       Date:  2008-05       Impact factor: 2.388

8.  Visual detection of cysteine and homocysteine.

Authors:  Oleksandr Rusin; Nadia N St Luce; Rezik A Agbaria; Jorge O Escobedo; Shan Jiang; Isiah M Warner; Fareed B Dawan; Kun Lian; Robert M Strongin
Journal:  J Am Chem Soc       Date:  2004-01-21       Impact factor: 15.419

9.  Progress toward red and near-infrared (NIR) emitting saccharide sensors.

Authors:  Martha Sibrian-Vazquez; Jorge O Escobedo; Mark Lowry; Robert M Strongin
Journal:  Pure Appl Chem       Date:  2012-04-29       Impact factor: 2.453

10.  Direct detection of homocysteine.

Authors:  Weihua Wang; Jorge O Escobedo; Candace M Lawrence; Robert M Strongin
Journal:  J Am Chem Soc       Date:  2004-03-24       Impact factor: 15.419

  10 in total

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