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.
The syntheses of 4-C-Me-DAB [n class="Chemical">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.
Authors: C Norez; C Vandebrouck; J Bertrand; S Noel; E Durieu; N Oumata; H Galons; F Antigny; A Chatelier; P Bois; L Meijer; F Becq Journal: Br J Pharmacol Date: 2014-11 Impact factor: 8.739
Authors: Lawrence D Harris; Rajesh K Harijan; Rodrigo G Ducati; Gary B Evans; Brett M Hirsch; Vern L Schramm Journal: ACS Chem Biol Date: 2017-12-14 Impact factor: 5.100
Authors: David M Campkin; Yuna Shimadate; Barbara Bartholomew; Paul V Bernhardt; Robert J Nash; Jennette A Sakoff; Atsushi Kato; Michela I Simone Journal: Molecules Date: 2022-05-26 Impact factor: 4.927
Authors: Sarah F Jenkinson; Loren L Parry; Francis X Wilson; George W J Fleet; David J Watkin Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-08-31
Authors: Anna Esposito; Daniele D'Alonzo; Maria De Fenza; Eliana De Gregorio; Anna Tamanini; Giuseppe Lippi; Maria Cristina Dechecchi; Annalisa Guaragna Journal: Int J Mol Sci Date: 2020-05-09 Impact factor: 5.923