ArticleTetrahedron letters2011
4-C-Me-DAB and 4-C-Me-LAB - enantiomeric alkyl-branched pyrrolidine iminosugars - are specific and potent α-glucosidase inhibitors; acetone as the sole protecting group.
Article in Tetrahedron letters, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Borylated 2,3,4,5-Tetrachlorophthalimide and Their 2,3,4,5-Tetrachlorobenzamide Analogues: Synthesis, Their Glycosidase Inhibition and Anticancer Properties in View to Boron Neutron Capture Therapy.Molecules (Basel, Switzerland) · 2022Article
- Pharmacological Chaperone Therapy for Pompe Disease.Molecules (Basel, Switzerland) · 2021Review
- Synthesis and Therapeutic Applications of Iminosugars in Cystic Fibrosis.International journal of molecular sciences · 2020Review
- Synthesis and Glycosidase Inhibition of Broussonetine M and Its Analogues.Molecules (Basel, Switzerland) · 2019Article
- Synthesis of bis-Phosphate Iminoaltritol Enantiomers and Structural Characterization with Adenine Phosphoribosyltransferase.ACS chemical biology · 2018Article
- Roscovitine is a proteostasis regulator that corrects the trafficking defect of F508del-CFTR by a CDK-independent mechanism.British journal of pharmacology · 2014Article
- Cystic fibrosis bronchial epithelial cells are lipointoxicated by membrane palmitate accumulation.PloS one · 2014Article
- 2-N-Benzyl-2,6-dide-oxy-2,6-imino-3,4-O-isopropyl-idene-3-C-methyl-d-allono-nitrile.Acta crystallographica. Section E, Structure reports online · 2012Article
- 6-De-oxy-3,4-O-isopropyl-idene-2-C-methyl-l-galactono-1,5-lactone.Acta crystallographica. Section E, Structure reports online · 2011Article
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Authors and funding
12 authors.
Funding
Abstract
The syntheses of 4-C-Me-DAB [1,4-dideoxy-1,4-imino-4-C-methyl-d-arabinitol] from l-erythronolactone and of 4-C-Me-LAB [from d-erythronolactone] require only a single acetonide protecting group. The effect of pH on the NMR spectra of 4-C-Me-DAB [pK(a) of the salt around 8.4] is discussed and illustrates the need for care in analysis of both coupling constants and chemical shift. 4-C-Me-DAB (for rat intestinal sucrase K(i) 0.89 μM, IC(50) 0.41 μM) is a competitive - whereas 4-C-Me-LAB (for rat intestinal sucrase K(i) 0.95 μM, IC(50) 0.66 μM) is a non-competitive - specific and potent α-glucosidase inhibitor. A rationale for the α-glucosidase inhibition by DAB, LAB, 4-C-Me-DAB, 4-C-Me-LAB, and isoDAB - but not isoLAB - is provided. Both are inhibitors of endoplasmic reticulum (ER) resident α-glucosidase I and II.
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Registered trials
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