Polyhydroxyazepanes mimicking monosaccharides: Synthesis of an alpha-D-galacto-like iminoheptitol

Li, H. Q.; Breriot, Y.; Mallet, J. M.; Zhang, Y. M.; Rodriguez-Garcia, E.; Vogel, P.; Mari, S.; Jimenez-Barbero, J.; Sinay, P.

doi:10.3987/COM-04-S(P)45

Li, H. Q.; Breriot, Y.; Mallet, J. M.; Zhang, Y. M.; Rodriguez-Garcia, E.; Vogel, P.; Mari, S.; Jimenez-Barbero, J.; Sinay, P.

2004

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Abstract

The synthesis of three new examples of seven-membered ring iminoalditols, displaying an extra hydroxymethyl group on the ring compared to the previously reported polyhydroxylated azepanes, has been achieved from D-lyxonolactone. None of them, including the alpha-D-galacto-like azepane (7), showed significant glycosidase inhibition on green coffee bean alpha-galactosidase and other commercially available hydrolases.

Details

Title Polyhydroxyazepanes mimicking monosaccharides: Synthesis of an alpha-D-galacto-like iminoheptitol

Author(s) Li, H. Q. ; Breriot, Y. ; Mallet, J. M. ; Zhang, Y. M. ; Rodriguez-Garcia, E. ; Vogel, P. ; Mari, S. ; Jimenez-Barbero, J. ; Sinay, P.

Published in Heterocycles

Volume 64

Pages 65-74

Date 2004

ISSN 0385-5414

Keywords

Glycosidase inhibitors; 7-membered iminocyclitols; biological; evaluation; olefin metathesis; imino sugars; agents; ring; tetrahydroxyazepanes; configuration; glucosidase

Note Ecole Normale Super, Dept Chem, UMR 8642, F-75231 Paris 05, France. EPFL, Swiss Fed Inst Technol, Lab Glycochim & Synth Asymet, BCH, CH-1015 Lausanne, Switzerland. CSIC, Ctr Invest Biol, E-28040 Madrid, Spain.

DOI https://doi.org/10.3987/COM-04-S(P)45

Other identifier(s) DAR: 6114
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Laboratories LGSA

Record Appears in Scientific production and competences > SB - School of Basic Sciences > SB Archives > LGSA - Laboratory of Glycochemistry and Asymmetric Synthesis
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Record creation date 2005-11-09