Design, synthesis, and enzymatic property of a sulfur-substituted analogue of trigalacturonic acid.

A sulfur-substituted analogue of trigalacturonic acid (3) was synthesized. The synthesis features the application of 3-cyano-3-(tert-butyldimethylsilyl)oxypropylthioether (CSP) as a novel protective group for thiols. This analogue was designed with the expectation that it would be a stable analogous substrate for endo-polygalacturonase isolated from Stereum purpureum based on computer modeling experiments. Surface plasmon resonance experiments revealed that 3 forms a stable complex with the target enzyme.

[1]  M. Evans.  Methyl 4,6-O-benzylidene-α- and -β-d-glucosides , 1972 .

[2]  S. Hanessian.  Preparative carbohydrate chemistry , 1997 .

[3]  Y Hasegawa,et al.  Kinetic measurement of the interaction between an oligosaccharide and lectins by a biosensor based on surface plasmon resonance. , 1994, European journal of biochemistry.

[4]  T. Gidenne.  Fibres in rabbit feeding for digestive troubles prevention: respective role of low-digested and digestible fibre , 2003 .

[5]  H. Overkleeft,et al.  Thioglycuronides: synthesis and application in the assembly of acidic oligosaccharides. , 2004, Organic letters.

[6]  Karl N. Kirschner,et al.  Solvent interactions determine carbohydrate conformation , 2001, Proceedings of the National Academy of Sciences of the United States of America.

[7]  T. Okuno,et al.  Determination of glycosylation sites, disulfide bridges, and the C-terminus of Stereum purpureum mature endopolygalacturonase I by electrospray ionization mass spectrometry. , 2000, European journal of biochemistry.

[8]  V. Shevchik,et al.  AN EFFICIENT AND HIGHLY STEREOSELECTIVE ALPHA (14) GLYCOSYLATION BETWEEN TWO D-GALACTURONIC ACID ESTER DERIVATIVES , 1997 .

[9]  T. Nakatsu,et al.  Crystallization and preliminary X-ray study of endopolygalacturonase from the pathogenic fungus Stereum purpureum. , 2001, Acta crystallographica. Section D, Biological crystallography.

[10]  W. Haskell,et al.  Long-term effects of water-soluble dietary fiber in the management of hypercholesterolemia in healthy men and women. , 1997, The American journal of cardiology.

[11]  Minoru Saito,et al.  Molecular dynamics simulations of proteins in solution: Artifacts caused by the cutoff approximation , 1994 .

[12]  S. Ring,et al.  Material properties of concentrated pectin networks. , 2004, Carbohydrate research.

[13]  Biao Yu,et al.  Synthesis of a S-linked heparan sulfate trisaccharide as the substrate mimic of heparanase , 2005 .

[14]  H. Driguez,et al.  Triphenylmethanethiol. An useful reagent in the synthesis of 1,2-cis-1-thioglycoses , 1990 .