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2,5-Deoxyfructosazine, a d-glucosamine derivative, inhibits T-cell interleukin-2 production better than d-glucosamine.

Zhu A, Huang JB, Clark A, Romero R, Petty HR

Department of Ophthalmology and Visual Sciences, The University of Michigan Medical School, Ann Arbor, MI 48105, United States.

d-Glucosamine has been widely reported to have immunosuppressive actions on neutrophils, lymphocytes, and other cells of the immune system. However, under conditions used in biological experiments (e.g., neutral pH, and phosphate buffers), we have found that d-glucosamine self-reacts to form 2,5-deoxyfructosazine [2-(d-arabino-tetrahydroxybutyl)-5-(d-erythro-2,3,4-trihydroxybutyl)pyrazine] (1) and 2,5-fructosazine [2,5-bis(d-arabino-tetrahydroxybutyl)pyrazine] (2). When tested for bioactivity at nontoxic concentrations, these d-glucosamine derivatives were more effective inhibitors of IL-2 release from PHA-activated T cells than d-glucosamine. Hence, fructosazines constitute a novel class of immunomodulators.

Published 23 November 2007 in Carbohydr Res, 342(18): 2745-9.
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