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Literature DB >> 21985023

Inhibition of nonmammalian glycosidases by azetidine iminosugars derived from stable 3,5-di-O-triflates of pentoses.

Gabriel M J Lenagh-Snow¹, Noelia Araujo, Sarah F Jenkinson, Catherine Rutherford, Shinpei Nakagawa, Atsushi Kato, Chu-Yi Yu, Alexander C Weymouth-Wilson, George W J Fleet.

Abstract

Efficient ring closure of stable crystalline 3,5-di-O-triflates of pentofuranosides with amines to form azetidines allowed preliminary evaluation of four-ring iminosugars as glycosidase inhibitors; significant and specific inhibition of nonmammalian α-glucosidases is shown by L-xylo- and L-arabino-iminosugar azetidines.

Entities: Chemical

Mesh：

Substances：

Year: 2011 PMID： 21985023 DOI： 10.1021/ol2024482

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

6 in total

1. Synthesis and evaluation of eight- and four-membered iminosugar analogues as inhibitors of testicular ceramide-specific glucosyltransferase, testicular β-glucosidase 2, and other glycosidases.

Authors: Jae Chul Lee; Subhashree Francis; Dinah Dutta; Vijayalaxmi Gupta; Yan Yang; Jin-Yi Zhu; Joseph S Tash; Ernst Schönbrunn; Gunda I Georg
Journal: J Org Chem Date: 2012-03-20 Impact factor: 4.354

2. Oxidative allene amination for the synthesis of azetidin-3-ones.

Authors: Eileen G Burke; Jennifer M Schomaker
Journal: Angew Chem Int Ed Engl Date: 2015-08-19 Impact factor: 15.336

3. Design and synthesis of nucleolipids as possible activated precursors for oligomer formation via intramolecular catalysis: stability study and supramolecular organization.

Authors: Kishore Lingam Gangadhara; Puneet Srivastava; Jef Rozenski; Henri-Philippe Mattelaer; Volker Leen; Wim Dehaen; Johan Hofkens; Eveline Lescrinier; Piet Herdewijn
Journal: J Syst Chem Date: 2014-12-09

Inhibition of nonmammalian glycosidases by azetidine iminosugars derived from stable 3,5-di-O-triflates of pentoses.

1. Synthesis and evaluation of eight- and four-membered iminosugar analogues as inhibitors of testicular ceramide-specific glucosyltransferase, testicular β-glucosidase 2, and other glycosidases.

2. Oxidative allene amination for the synthesis of azetidin-3-ones.

3. Design and synthesis of nucleolipids as possible activated precursors for oligomer formation via intramolecular catalysis: stability study and supramolecular organization.

4. First total synthesis of kipukasin A.

5. N-Benzyl-3,5-dide-oxy-3,5-imino-1,2-O-isopropyl-idene-β-l-lyxofuran-ose.

6. 1-O-Benzyl-2,3-O-iso-propyl-idene-6-O-tosyl-α-l-sorbo-furan-ose.