Synthesis and evaluation of galacto-noeurostegine and its 2-deoxy analogue as glycosidase inhibitors

2015 ◽  
Vol 13 (29) ◽  
pp. 7979-7992 ◽  
Author(s):  
Stéphane Salamone ◽  
Lise L. Clement ◽  
Agnete H. Viuff ◽  
Ole Juul Andersen ◽  
Frank Jensen ◽  
...  
Keyword(s):  
Aspergillus Oryzae ◽  
Glycosidase Inhibitors ◽  
Glycosidase Inhibitor

An epimer of the known glycosidase inhibitor noeurostegine, galacto-noeurostegine, was synthesised in 21 steps from levoglucosan and found to be a potent, competitive and highly selective galactosidase inhibitor of Aspergillus oryzae β-galactosidase.

Synthesis of Selenium Analogues of the Naturally Occurring Glycosidase Inhibitor Salacinol and Their Evaluation as Glycosidase Inhibitors†

2002 ◽  
Vol 124 (28) ◽  
pp. 8245-8250 ◽  
Author(s):  
Blair D. Johnston ◽  
Ahmad Ghavami ◽  
Morten T. Jensen ◽  
Birte Svensson ◽  
B. Mario Pinto
Keyword(s):  
Glycosidase Inhibitors ◽  
Naturally Occurring ◽  
Glycosidase Inhibitor

scholarly journals Thio-β-D-glucosides: Synthesis and Evaluation as Glycosidase Inhibitors and Activators

2014 ◽  
Vol 2014 ◽  
pp. 1-8 ◽  
Author(s):  
Andrey V. Samoshin ◽  
Irina A. Dotsenko ◽  
Nataliya M. Samoshina ◽  
Andreas H. Franz ◽  
Vyacheslav V. Samoshin
Keyword(s):  
Aspergillus Oryzae ◽  
Selective Inhibition ◽  
Glycosidase Inhibitors ◽  
Penicillium Canescens ◽  
Potential Inhibitors

Structurally simple 1-thio-β-D-glucopyranosides were synthesized and tested as potential inhibitors toward several fungal glycosidases from Aspergillus oryzae and Penicillium canescens. Significant selective inhibition was observed for α- and β-glucosidases, while a weak to moderate activation for α- and β-galactosidases.

Sugar hydrazide imides: a new family of glycosidase inhibitors

2017 ◽  
Vol 15 (41) ◽  
pp. 8709-8712 ◽  
Author(s):  
Emil Lindbäck ◽  
Óscar Lopéz ◽  
Ådne Tobiesen ◽  
José G. Fernández-Bolaños ◽  
Magne O. Sydnes
Keyword(s):  
Glycosidase Inhibitors ◽  
New Family ◽  
New Type ◽  
Glycosidase Inhibitor ◽  
Micromolar Range

We present a new type of glycosidase inhibitor including a unique hydrazide imide moiety, which displays inhibition in the low micromolar range.

The synthesis of protected 5-azido-5-deoxy-D-glucononitriles as precursors of glycosidase inhibitors

1990 ◽  
Vol 68 (2) ◽  
pp. 317-322 ◽  
Author(s):  
P. Bird ◽  
D. H. Dolphin ◽  
S. G. Withers
Keyword(s):  
Amino Sugars ◽  
Glycosidase Inhibitors ◽  
Glycosidase Inhibitor

The successful syntheses of 5-azido-2,3,4,6-tetra-O-benzyl-5-deoxy-D-glucononitrile and 2,3,4,6-tetra-O-benzyl-5-deoxy-5-trifluoroacetamido-D-glucononitrile starting from D-glucose are described. Unsuccessful attempts were made to convert these two compounds into a protected 5-amino-5-deoxy-D-glucononitrile and to subsequently cyclize them to an amidine analogue of glucose as a possible glycosidase inhibitor. Keywords: synthesis, amino-sugars, glycosidase inhibitors.

Synthesis of zwitterionic selenonium and sulfonium sulfates from D-mannose as potential glycosidase inhibitors

2006 ◽  
Vol 84 (4) ◽  
pp. 497-505 ◽  
Author(s):  
Hui Liu ◽  
B Mario Pinto
Keyword(s):  
Membered Ring ◽  
The Novel ◽  
Glycosidase Inhibitors ◽  
Naturally Occurring ◽  
Structure Activity ◽  
Glycosidase Inhibitor ◽  
Ring Core

Four chain-extended analogues of the naturally occurring glycosidase inhibitor salacinol were synthesized for structure–activity studies with different glycosidase enzymes. The syntheses involved the reaction of isopropylidene-protected 1,4-thio- and 1,4-seleno-D-talitols and 1,5-thio- and 1,5-seleno-L-gulitols, derived from D-mannose, with a benzylidene- and isopropylidene-protected 1,3-cyclic sulfate, also derived from D-mannose. Deprotection of the products afforded the novel selenonium and sulfonium sulfates composed of heterocyclic five- and six-membered ring core structures with pendant polyhydroxylated, acyclic chains of six carbon atoms.Key words: glycosidase inhibitors, zwitterionic selenonium and sulfonium sulfates, cyclic sulfate

scholarly journals Selective Metabolism of Glycosidase Inhibitors by a Specialized Moth Feeding on Hyacinthoides non-scripta Flowers

2008 ◽  
Vol 3 (1) ◽  
pp. 1934578X0800300
Author(s):  
Alison A. Watson ◽  
Ana L. Winters ◽  
Sarah A. Corbet ◽  
Catherine Tiley ◽  
Robert J. Nash
Keyword(s):  
The Other ◽  
Glycosidase Inhibitors ◽  
Glucosidase Inhibitor ◽  
Glycosidase Inhibitor

The British moth Eana incanana (Tortricidae) has been found to selectively metabolize the glycosidase inhibitor 2 R, 3 R, 4 R, 5 R-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine (DMDP), whereas it excretes related alkaloids from Hyacinthoides non-scripta (Hyacinthaceae). Very few native animals feed on H. non-scripta, but the larvae of E. incanana are specialized herbivores feeding just on the buds and flowers destroying the ovary. DMDP is the major glucosidase inhibitor of H. non-scripta and the moth may overcome inhibition of digestive glucosidases by metabolizing the DMDP. The glucosidase enzymes of the caterpillar are inhibited by DMDP. The caterpillar excretes the other glycosidase inhibitors produced by this plant and the frass has increased concentrations of these alkaloids.

Synthesis of 1,4-anhydro-D-xylitol heteroanalogues of the naturally occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors

2002 ◽  
Vol 80 (8) ◽  
pp. 937-942 ◽  
Author(s):  
Ahmad Ghavami ◽  
Blair D Johnston ◽  
Matthew D Maddess ◽  
Sarah M Chinapoo ◽  
Morten T Jensen ◽  
...  
Keyword(s):  
Significant Inhibition ◽  
Nucleophilic Attack ◽  
Ammonium Ion ◽  
Aqueous Extracts ◽  
Glycosidase Inhibitors ◽  
Synthetic Strategy ◽  
Naturally Occurring ◽  
Glycosidase Inhibitor ◽  
Salacia Reticulata

The syntheses of two 1,4-anhydro-D-xylitol heteroanalogues (8 and 9) of the naturally occurring sulfonium ion, salacinol (3), containing a sulfur or nitrogen atom in the ring are described. Salacinol (3) is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of Type 2 diabetes. The synthetic strategy relies on the nucleophilic attack of sulfur or nitrogen analogues of 1,4-anhydro-D-xylitol at the least-hindered carbon of 2,4-O-benzylidene-L-erythritol-1,3-cyclic sulfate. The sulfonium ion 8 inhibited barley-α-amylase (AMY1) and porcine pancreatic-α-amylase (PPA), with Ki values of 109 ± 11 and 55 ± 5 µM, respectively. In contrast, the ammonium ion 9 showed no significant inhibition of either AMY1 or PPA. Compounds 8 and 9 also showed no significant inhibition of glucoamylase.Key Words: glycosidase inhibitors, salacinol analogues, anhydro-D-xylitol heteroanalogues, enzyme inhibition.

Supramolecular azasugar clusters based on an amphiphilic fatty-acid-deoxynojirimycin derivative as multivalent glycosidase inhibitors

2019 ◽  
Vol 7 (9) ◽  
pp. 1379-1383 ◽  
Author(s):  
Min Li ◽  
Ke-Rang Wang ◽  
Jian-Xing Yang ◽  
Ya-Tong Peng ◽  
Yi-Xuan Liu ◽  
...  
Keyword(s):  
Fatty Acid ◽  
Glycosidase Inhibitors ◽  
Glycosidase Inhibitor

A novel supramolecular multivalent glycosidase inhibitor was constructed based on the amphiphilic deoxynojirimycin derivative FA-DNJ.

Koji mold (Aspergillus oryzae)

AccessScience ◽  
2015 ◽  
Keyword(s):  
Aspergillus Oryzae ◽  
Koji Mold
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