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New fluorescent amino carbohydrate derivatives
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1  Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Apartado de Correos No. 1203, 41071 Sevilla, Spain. Fax: +34954624960; Tel: +34954556868; E-mail:

Abstract: The interest of fluorescent carbohydrates is due to wide applications in biology and environmental technology. For example, water soluble glucose based imino-anthracenyl derivatives have been shown to recognize specifically Hg2+ (which is highly toxic and causes DNA damage and impair mitosis) by switch-on fluorescence.[1] Fluorescence is a powerful technique as a consequence of its highly sensible and specific detection methods. [2],[3] With the aim to generate new derivatives with biological, pharmacological and technological properties, we design the here presented compounds using as diversity point (see Scheme), the amino group. We have selected coumarins as chromophore units (CU), due to their demonstrated anticoagulant activity and easy availability. On the other hand, fluorescent aldehydes have been chosen as fluorescence sources for their chemosensor potential activity in a wide variety of fields. We report here on new fluorescent derivatives of D-glucosamine (1) previous protection of its hydroxyl groups. These derivatives having general structures 2 and 3, have been prepared in good yields by: a) nucleophilic attack of the amino group to activated carboxycoumarins, and b) by reductive amination, respectively. We thank the AECID (Projects A/023577/09 and A/040322/10) and the \'Junta de Andalucía\' (FQM 142 and Project P09-AGR-4597) for financial support. [1] Mitra, A.; Mittal, K. A. and Rao, P. C. Chem. Comm., 2011, 47, 2565 and references therein. [2] Lee, D.Y.; Singh, N. and Jang, D. O. Tetrahedron Lett. 2010, 51, 1103 [3] a) Rettig, W. Applied Fluorescence in Chemistry, Biology and Medicine; Springer: New York, 1999. b) Christensen, L.; Norgaard, R.; Bro, S. and Engelsen, B. Chem. Rev. 2006, 106, 1979.