Visual chiral recognition of mandelic acid enantiomers with L-tartaric acid-capped gold nanoparticles as colorimetric probes

Sensors and Actuators, B: Chemical

Volumn 215, Issue , 2015, Pages 504-509

  Song, Guoxin ^a   Xu, Chunli ^a   Li, Baoxin ^a  

^a SHAANXI NORMAL UNIVERSITY   (China)

Author keywords

Chiral recognition; Colorimetric probes; Gold nanoparticles; Visual detection

Indexed keywords

COLOR; ENANTIOMERS; FIBER OPTIC SENSORS; GOLD; METAL NANOPARTICLES; NANOPARTICLES; ORGANIC ACIDS; PROBES;

CHIRAL MODIFICATION; CHIRAL RECOGNITION; COLORIMETRIC PROBES; ENANTIOMERIC EXCESS; GOLD NANOPARTICLES; L-TARTARIC ACIDS; MANDELIC ACID ENANTIOMERS; VISUAL DETECTION;

COLORIMETRY;

EID: 84928551810     PISSN: 09254005     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.snb.2015.03.109     Document Type: Article

References (38)

1. E.L. Izake Chiral discrimination and enantioselective analysis of drugs: an overview J. Pharm. Sci. 96 2007 1659 1676
2. J.V. Burda, K. Ariga, and J.P. Hill NMR spectroscopic detection of chirality and enantiopurity in referenced systems without formation of diastereomers Nat. Commun. 4 2013 2188
3. L. Wei, L. Yi, F. Song, C. Wei, B.-F. Wang, and Z. Xi FRET ratiometric probes reveal the chiral-sensitive cysteine-dependent H2S production and regulation in living cells Sci. Rep. 4 2014 4521
4. J. Labuta, Z. Futera, S. Ishihara, H. Kourilová, Y. Tateyama, K. Ariga, and J.P. Hill Chiral guest binding as a probe of macrocycle dynamics and tautomerism in a conjugated tetrapyrrole J. Am. Chem. Soc. 136 2014 2112 2118
5. M.L. Tang, J. Zhang, S.L. Zhuang, and W.P. Liu Development of chiral stationary phases for high-performance liquid chromatographic separation Trends Anal. Chem. 39 2012 180 194
6. T.J. Ward, and K.D. Ward Chiral separations: a review of current topics and trends Anal. Chem. 84 2012 626 635
7. X. Zhang, J. Yin, and J. Yoon Recent advances in development of chiral fluorescent and colorimetric sensors Chem. Rev. 114 2014 4918 4959
8. T. Tu, W. Fang, X. Bao, X. Li, and K.H. Dötz Visual chiral recognition through enantioselective metallogel collapsing: synthesis, characterization, and application of platinum-steroid low-molecular-mass gelators Angew. Chem. Int. Ed. 50 2011 6601 6605
9. L. Zhang, C. Xu, C. Liu, and B. Li Visual chiral recognition of tryptophan enantiomers using unmodified gold nanoparticles as colorimetric probes Anal. Chim. Acta 809 2014 123 127
10. C. Ding, A. Zhu, and Y. Tian Functional surface engineering of C-dots for fluorescent biosensing and in vivo bioimaging Acc. Chem. Res. 47 2014 20 30
11. K. Ariga, Y. Yamauchi, G. Rydzek, Q. Ji, Y. Yonamine, K.C.-W. Wu, and J.P. Hill Layer-by-layer nanoarchitectonics: invention, innovation, and evolution Chem. Lett. 43 2014 36 68
12. S. Ishihara, J. Labuta, W.V. Rossom, D. Ishikawa, K. Minami, J.P. Hill, and K. Ariga Porphyrin-based sensor nanoarchitectonics in diverse physical detection modes Phys. Chem. Chem. Phys. 16 2014 9713 9746
13. D.A. Giljohann, D.S. Seferos, W.L. Daniel, M.D. Massich, P.C. Patel, and C.A. Mirkin Gold nanoparticles for biology and medicine Angew. Chem. Int. Ed. 49 2010 3280 3294
14. Y. Song, W. Wei, and X. Qu Colorimetric biosensing using smart materials Adv. Mater. 23 2011 4215 4236
15. K. Saha, S.S. Agasti, C. Kim, X.N. Li, and V.M. Rotello Gold nanoparticles in chemical and biological sensing Chem. Rev. 112 2012 2739 2779
16. H. Su, Q. Zheng, and H. Li Colorimetric detection and separation of chiral tyrosine based on N-acetyl-L-cysteine modified gold nanoparticles J. Mater. Chem. 22 2012 6546 6548
17. S.H. Seo, S. Kim, and M.S. Han Gold nanoparticle-based colorimetric chiral discrimination of histidine: application to determining the enantiomeric excess of histidine Anal. Methods 6 2014 73 76
18. M. Zhang, and B.C. Ye Colorimetric chiral recognition of enantiomers using the nucleotide-capped silver nanoparticles Anal. Chem. 83 2011 1504 1509
19. Y. Sun, L. Zhang, and H.B. Li Chiral colorimetric recognition of amino acids based on silver nanoparticle clusters New J. Chem. 36 2012 1442 1444
20. D. Xiong, M.L. Chen, and H.B. Li Synthesis of para-sulfonatocalix[4]arene-modified silver nanoparticles as colorimetric histidine probes Chem. Commun. 44 2008 880 882
21. G. Lautrette, B. Kauffmann, Y. Ferrand, C. Aube, N. Chandramouli, D. Dubreuil, and I. Huc Structure elucidation of host-guest complexes of tartaric and malic acids by quasi-racemic crystallography Angew. Chem. Int. Ed. 52 2013 11517 11520
22. L. Yao, X.M. Lu, S.S. Chen, and J.J. Watkins Formation of helical phases in achiral block copolymers by simple addition of small chiral additives Macromolecules 47 2014 6547 6553
23. N. Ôi, H. Kitahara, and F. Aoki Enantiomer separation by high-performance liquid chromatography with (R,R)-tartaric acid mono-amide derivatives as bifunctional chiral selectors J. Chromatogr. A 666 1994 457 462
24. K.C. Grabar, R.G. Freeman, M.B. Hommer, and M.J. Natan Preparation and characterization of Au colloid monolayers Anal. Chem. 67 1995 735 743
25. Y.Z. Fu, L.L. Wang, Q. Chen, and J. Zhou Enantioselective recognition of chiral mandelic acid in the presence of Zn(II) ions by L-cysteine-modified electrode Sens. Actuators B 155 2011 140 144
26. E. Zor, A. Saf, H. Bingol, and M. Ersoz Voltammetric discrimination of mandelic acid enantiomers Anal. Biochem. 449 2014 83 89
27. R.C. Jin, G.S. Wu, Z. Li, C.A. Mirkin, and G.C. Schatz What controls the melting properties of DNA-linked gold nanoparticle assemblies? J. Am. Chem. Soc. 125 2003 1643 1654
28. X.H. Ji, X.N. Song, J. Li, Y.B. Bai, W.S. Yang, and X.G. Peng Size control of gold nanocrystals in citrate reduction: the third role of citrate J. Am. Chem. Soc. 129 2007 13939 13948
29. H.M. Zakaria, A. Shah, M. Konieczny, J.A. Hoffmann, A.J. Nijdam, and M.E. Reeves Small molecule- and amino acid-induced aggregation of gold nanoparticles Langmuir 29 2013 7661 7673
30. R.E. Gawley Do the terms "% ee" and "% de" make sense as expressions of stereoisomer composition or stereoselectivity? J. Org. Chem. 71 2006 2411 2416
31. C. Liu, B. Li, and C. Xu Colorimetric chiral discrimination and determination of enantiometric excess of D/L-tryptophan using silver nanoparticles Microchim. Acta 181 2014 1407 1413
32. S. Wang, W. Chen, A.L. Liu, L. Hong, H.H. Deng, and X.H. Lin Comparison of the peroxidase-like activity of unmodified, amino-modified, and citrate-capped gold nanoparticles ChemPhysChem 13 2012 1199 1204
33. I.-I.S. Lim, D. Mott, M.H. Engelhard, Y. Pan, S. Kamodia, J. Luo, P.N. Njoki, S. Zhou, L. Wang, and C.J. Zhong Interparticle chiral recognition of enantiomers: a nanoparticle-based regulation strategy Anal. Chem. 81 2009 689 698
34. C. Han, and H. Li Chiral recognition of amino acids based on cyclodextrin-capped quantum dots Small 4 2008 1344 1350
35. Y. Zhang, B. Li, and X. Chen Simple and sensitive detection of dopamine in the presence of high concentration of ascorbic acid using gold nanoparticles as colorimetric probes Microchim. Acta 168 2010 107 113
36. H. Yao, H. Kojima, S. Sato, and K. Kimura Interparticle spacing control in the superlattices of carboxylic acid-capped gold nanoparticles by hydrogen-bonding mediation Langmuir 20 2004 10317 10323
37. I.M.G. Cowie, V. Arrighi, and E.-A. McGonigle Enthalpy relaxation in poly(4-hydroxystyrene)/poly(methyl methacrylate) blends Macromol. Chem. Phys. 206 2005 767 776
38. X. Hou, D. Gao, J. Yan, Y. Ma, K. Liu, and Y. Fang Novel dimeric cholesteryl derivatives and their smart thixotropic gels Langmuir 27 2011 12156 12163