Bioorganic & Medicinal Chemistry 2007-06-15

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?

Carine Chevrier, Albert Defoin, Céline Tarnus

Index: Bioorg. Med. Chem. 15(12) , 4125-35, (2007)

Full Text: HTML

Abstract

Cyclic D- and L-4-aminothreose were synthesised from ethyl D- and L-tartrate, respectively. D-aminothreose was a potent inhibitor of alpha-glucosidase and of alpha-mannosidase. From the glycosidase inhibition potencies of the four 4-amino-4-deoxy-tetroses, the contribution of binding of each functionality of the 5 and 6 membered ring amino-sugars towards the various glycosidases is discussed.

Related Compounds

  • D-(-)-threose
  • L-(+)-threose

Related Articles:

The silicate-mediated formose reaction: bottom-up synthesis of sugar silicates.

2010-02-19

[Science 327(5968) , 984-6, (2010)]

Formation of furan and methylfuran from ascorbic acid in model systems and food.

2007-01-01

[Food Addit. Contam. 24 Suppl 1 , 122-35, (2007)]

Nonenzymatic oligomerization of RNA by TNA templates.

2006-12-07

[Org. Lett. 8(25) , 5809-11, (2006)]

Kinetic characterization and comparison of various protein crosslinking reagents for matrix modification.

2010-04-01

[J. Mater. Sci. Mater. Med. 21(4) , 1175-81, (2010)]

Efficient asymmetric organocatalytic formation of erythrose and threose under aqueous conditions.

2010-07-14

[Chem. Commun. (Camb.) 46(26) , 4776-8, (2010)]

More Articles...