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 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

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.

Design and synthesis of selenonium and sulfonium ions related to the naturally occurring glucosidase inhibitor salacinol

2006 ◽  
Vol 84 (10) ◽  
pp. 1351-1362 ◽  
Author(s):  
Hui Liu ◽  
B Mario Pinto
Keyword(s):  
Nucleophilic Attack ◽  
Significant Activity ◽  
The Novel ◽  
Glycosidase Inhibitors ◽  
Design And Synthesis ◽  
Glucosidase Inhibitor ◽  
Naturally Occurring ◽  
Sulfonium Ions ◽  
Stereogenic Centers ◽  
Cyclic Sulfates

Four series of analogues of the naturally occurring glucosidase inhibitor salacinol were synthesized for structure–activity studies with different glycosidase enzymes. The target zwitterionic compounds were synthesized by means of nucleophilic attack at the least-hindered carbon atom of the 1,3-cyclic sulfates derived from D-glucose and D-mannose by the isopropylidene-protected 1,4-anhydro-4-thio- and seleno-D-allitols and the 4-thio- and seleno-L-allitols. Deprotection of the coupled products afforded the novel sulfonium and selenonium ions containing polyhy droxylated acyclic chains of four and six carbons, with different stereochemistry at the stereogenic centers and with 1,4-anhydro-4-seleno or 4-thio-D- or L- alditol heterocyclic rings. The compounds showed no significant activity against recombinant human maltase glucoamylase (MGA), a critical intestinal glucosidase involved in the processing of oligosaccharides of glucose into glucose itself.Key words: glycosidase inhibitors, zwitterionic, selenonium salts, sulfonium salts, cyclic sulfates, L-ascorbic acid, D-gulonic-γ-lactone.

Improved Syntheses of the Naturally Occurring Glycosidase Inhibitor Salacinol

Synlett ◽  
2003 ◽  
Vol 2003 (09) ◽  
Author(s):  
B. Pinto ◽  
Ahmad Ghavami ◽  
Kashinath Sadalapure ◽  
Blair Johnston ◽  
Mercedes Lobera ◽  
...  
Keyword(s):  
Naturally Occurring ◽  
Glycosidase Inhibitor

Naturally Occurring Glycosidase Inhibitors

2007 ◽  
pp. 407-420 ◽  
Author(s):  
Robert Nash
Keyword(s):  
Glycosidase Inhibitors ◽  
Naturally Occurring

Improved Syntheses of the Naturally Occurring Glycosidase Inhibitor Salacinol.

ChemInform ◽  
2003 ◽  
Vol 34 (48) ◽  
Author(s):  
Ahmad Ghavami ◽  
Kashinath S. Sadalapure ◽  
Blair D. Johnston ◽  
Mercedes Lobera ◽  
Barry B. Snider ◽  
...  
Keyword(s):  
Naturally Occurring ◽  
Glycosidase Inhibitor

Synthesis of 2-amido, 2-amino, and 2-azido derivatives of the nitrogen analogue of the naturally occurring glycosidase inhibitor salacinol and their inhibitory activities against O-GlcNAcase and NagZ enzymes

2008 ◽  
Vol 343 (10-11) ◽  
pp. 1766-1777 ◽  
Author(s):  
Niloufar Choubdar ◽  
Ramakrishna G. Bhat ◽  
Keith A. Stubbs ◽  
Scott Yuzwa ◽  
B. Mario Pinto
Keyword(s):  
Naturally Occurring ◽  
Glycosidase Inhibitor ◽  
Inhibitory Activities ◽  
Derivatives Of

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.

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