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 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

Synthesis and evaluation of amino-threoses in d- and l-series: Are five membered ring amino-sugars more potent glycosidase inhibitors than the six membered ones?

2007 ◽  
Vol 15 (12) ◽  
pp. 4125-4135 ◽  
Author(s):  
Carine Chevrier ◽  
Albert Defoin ◽  
Céline Tarnus
Keyword(s):  
Membered Ring ◽  
Amino Sugars ◽  
Glycosidase Inhibitors

Plagiarizing Plants: Amino Sugars as a Class of Glycosidase Inhibitors

2007 ◽  
pp. 112-125 ◽  
Author(s):  
George W. J. Fleet ◽  
Linda E. Fellows ◽  
Bryan Winchester
Keyword(s):  
Amino Sugars ◽  
Glycosidase Inhibitors

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.

Evaluation of 6-Deoxy-amino-sugars as Potent Glycosidase Inhibitors. Importance of the CH2 OH(6) Group for Enzyme-Substrate Interaction

2017 ◽  
Vol 2 (4) ◽  
pp. 1484-1490 ◽  
Author(s):  
Hervé Sarazin ◽  
Sandrine Prudent ◽  
Albert Defoin ◽  
Céline Tarnus
Keyword(s):  
Amino Sugars ◽  
Glycosidase Inhibitors ◽  
Substrate Interaction ◽  
Enzyme Substrate

scholarly journals Change in specificity of glycosidase inhibition by N-alkylation of amino sugars

1989 ◽  
Vol 258 (2) ◽  
pp. 613-615 ◽  
Author(s):  
S al Daher ◽  
G Fleet ◽  
S K Namgoong ◽  
B Winchester
Keyword(s):  
Inhibitory Activity ◽  
Human Liver ◽  
Amino Sugar ◽  
Amino Sugars ◽  
Weak Inhibitor ◽  
First Report ◽  
Glycosidase Inhibitor ◽  
Ring Nitrogen ◽  
Glycosidase Inhibition

The synthetic amino sugar 1,4-dideoxy-1,4-imino-L-allitol (DIA) is a moderately good inhibitor of human liver alpha-D-mannosidases and a weak inhibitor of alpha-L-fucosidase, N-acetyl-beta-D-hexosaminidase and beta-D-mannosidase. Methylation of the ring nitrogen of DIA markedly decreases the inhibition of all the glycosidases except N-acetyl-beta-D-hexosaminidase. N-Benzylation of DIA essentially abolishes all inhibitory activity, except towards alpha-L-fucosidase, which is more strongly inhibited than by either DIA or N-methyl-DIA. This is the first report of a change of specificity of inhibition of a glycosidase inhibitor by substitution of the ring nitrogen.

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.

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.

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