Mitra, Atanu ; Chinta, Jugun Prakash ; Rao, Chebrolu P. (2010) 1-(D-Glucopyranosyl-2'-deoxy-2'-iminomethyl)-2-hydroxybenzene as chemosensor for aromatic amino acids by switch-on fluorescence Tetrahedron Letters, 51 (1). pp. 139-142. ISSN 0040-4039
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.tetlet.2009.10.105
Abstract
A glucose based C2-glyco-conjugate, that is, 1-(D-glucopyranosyl-2'-deoxy-2'-iminomethyl)-2-hydroxybenzene (L), has been synthesized in a high yield and characterized. Titration of L with all the 20 naturally occurring amino acids resulted in a large fluorescence intensity enhancement only in case of aromatic amino acids, that is, Phe, Trp, His, and Tyr and not with the others. This has been attributed to the initial formation of 1:1 hydrogen bonded complex followed by π-π interactions present between the aromatic moieties of such complexes as demonstrated by absorption and computational methods. Thus L has been able to recognize aromatic amino acids down to 1.5-3 ppm through switch-on fluorescence behavior.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | 1-(D-Glucopyranosyl-2'-deoxy-2'-iminomethyl)-2-hydroxybenzene; Recognition of Aromatic Amino Acids; Switch-on Fluorescence; Computational Calculations; H-bonded 1:1 Complex; π-π Interactions |
| ID Code: | 79172 |
| Deposited On: | 24 Jan 2012 15:31 |
| Last Modified: | 19 Apr 2012 06:44 |
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