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Concise Total Synthesis of Glucosepane by Cristian Draghici; Tina Wang; David A. Spiegel is a Medicine article available to read on EtoBox.

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Glucosepane is a structurally complex protein posttranslational modification that is believed to exist in all living organisms. Research in humans suggests that glucosepane plays a critical role in the pathophysiology of both diabetes and human aging, yet comprehensive biological investigations of this metabolite have been hindered by a scarcity of chemically homogeneous material available for study. Here we report the total synthesis of glucosepane, enabled by the development of a one-pot method for preparation of the nonaromatic 4H-imidazole tautomer in the core. Our synthesis is concise (eight steps starting from commercial materials), convergent, high-yielding (12% overall), and enantioselective. We expect that these results will prove useful in the art and practice of heterocyclic chemistry and beneficial for the study of glucosepane and its role in human health and disease.

Who reads Concise Total Synthesis of Glucosepane?

Author

Cristian Draghici; Tina Wang; David A. Spiegel

Publisher

American Association for the Advancement of Science (AAAS)

Published

2015

Language

EN

Field

Medicine (Social Sciences)