Synthesis of 1,6-Anhydro-2,3-di-O-farnesyl-5-O-([{phosphonomethyl}phosphinyl]methyl)-α-d-galactofuranose: A Zaragozic Acid-Presqualene Pyrophosphate Hybrid

A. R.P.M. Valentijn Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, P.O. Box 9502, 2300, RA, Leiden, The Netherlands

H. J.G. Broxterman Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, P.O. Box 9502, 2300, RA, Leiden, The Netherlands

G. A. van der Marel Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, P.O. Box 9502, 2300, RA, Leiden, The Netherlands

L. H. Cohen TNO Prevention and Health, Gaubius Laboratory, P.O. Box 2215, 2301, CE, Leiden, The Netherlands

J. H. van Boom Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, P.O. Box 9502, 2300, RA, Leiden, The Netherlands

Abstract

A multi-step synthesis of a new potential inhibitor (i.e., compound 2) of squalene synthase is described, starting from D-galactose. The title compound is a hybrid of presqualene pyrophopshate and the recently discovered zaragozic acids, which are picomolar competitive inhibitors of the enzyme squalene synthase.

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Synthesis of 1,6-Anhydro-2,3-di-O-farnesyl-5-O-([{phosphonomethyl}phosphinyl]methyl)-α-d-galactofuranose: A Zaragozic Acid-Presqualene Pyrophosphate Hybrid

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Synthesis of 1,6-Anhydro-2,3-di-O-farnesyl-5-O-([{phosphonomethyl}phosphinyl]methyl)-α-d-galactofuranose: A Zaragozic Acid-Presqualene Pyrophosphate Hybrid

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