D-mannonolactam amidrazone. A new mannosidase inhibitor that also inhibits the endoplasmic reticulum or cytoplasmic alpha-mannosidase.

Inhibitors of Carbohydrate-Processing Enzymes: Design and Synthesis of Sugar-Shaped Heterocycles

“…Besides jackbean α-man, 38 also inhibited mung bean α-man (IC 50 = 400 nM), fungal β-man (IC 50 = 150 nM), Golgi α-man I (IC 50 = 4 μM), and α-man II (IC 50 = 90−100 nΜ). It also proved to be the first potent inhibitor of the soluble (or endoplasmic reticulum) α-man, with an IC 50 of 1 μM . The latter triad of mannosidases constituted the principal mannose-processing pathway in the biosynthesis of glycoproteins.…”

“…It also proved to be the first potent inhibitor of the soluble (or endoplasmic reticulum) R-man, with an IC 50 of 1 µM. 43 The latter triad of mannosidases constituted the principal mannose-processing pathway in the biosynthesis of glycoproteins. A further test of D-mannoamidrazone (38) as an in vivo mannosidase inhibitor was performed in animal cell cultures using Madin-Darby canine kidney cells infected with influenza virus.…”

A Versatile Synthetic Strategy for the Preparation and Discovery of New Iminocyclitols as Inhibitors of Glycosidases

“…Enzymatic hydrolysis of the glycosidic bonds generally takes place via general acid−base catalyses that require two critical residues, a proton donor and a nucleophile (Figure ) . Five- or six-membered iminocyclitols carrying hydroxyl groups with specific orientation and a secondary amine have been used to mimic the shape and charge of the transition state of the reaction and have been shown to be potent inhibitors of such enzymes. 1a,,

1 Proposed mechanism and transition state of β-glucosidase-catalyzed reaction and representative structures of transition-state analogue inhibitors.

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Evaluating N-benzylgalactonoamidines as putative transition state analogs for β-galactoside hydrolysis

“…8,11 acetate buffer at 30 °C for the same amount of time. However, the glyconoamidine stability under alkaline conditions is debated in the literature, [9][10][11][12][13][14] and insufficient stability of 1d in conditions previously used for the preparation of microgels, i.e. 50 mM CAPS buffer at pH 10.5 and 72 °C, was noted.…”

“…Instrumentation 1 H and 13 C NMR spectra were recorded on a 400 MHz Bruker magnet with Z gradient and 5 mm broadband head using High resolution mass spectrometry data were obtained from samples that were mixed with acetonitrile containing 0.1% formic acid and injected into the source via syringe pump operating at 3 µL h −1 . The dry gas temperature was 180 °C, the dry gas flow was 5 L min −1 , and the nebulizing gas pressure was 1 bar.…”