Assembly of a three-dimensional array of glycoconjugates by combinatorial biocatalysis in nonaqueous media.

Glycoconjugates can be artificially synthesized by combinatorial biocatalysis. An example is given in this paper describing the construction of glycoconjugates array by using glycosidase and lipase in nonaqueous media. This array was started from glucose, with three aryl alcohols as the aglycone moiety of glycosides and five acids or esters as acyl donors for combinatorial acylation of glycosides, affording a three-dimensional array containing about 30 members with diverse structures. The array would be more abundant if more aglycones and acyl donors with other structures were filled in. Indeed, diverse classes of carbohydrates besides glucose can also be employed for generating diverse glycoconjugates due to their different roles in numerous physiological responses. The composition and distribution of the demonstration glycoconjugates array was detected and evaluated by HPLC-MS with electrospray ionization. And also, the distribution of the artificial array can be adjusted by changing the molar ratio of the auxiliary materials.

[1]  S. Riva Enzymatic modification of the sugar moieties of natural glycosides , 2002 .

[2]  Raymond A. Dwek,et al.  Glycobiology: Toward Understanding the Function of Sugars. , 1996, Chemical reviews.

[3]  Hans Mooibroek,et al.  Bio-refinery as the bio-inspired process to bulk chemicals. , 2007, Macromolecular bioscience.

[4]  Chi‐Huey Wong,et al.  Chemical, Enzymatic and Structural Studies in Molecular Glycobiology , 1997 .

[5]  U. Bornscheuer,et al.  Synthesis of aromatic n-alkyl-glucoside esters in a coupled β-glucosidase and lipase reaction , 1998, Biotechnology Letters.

[6]  F. Kolisis,et al.  Lipase-catalyzed esterification of rutin and naringin with fatty acids of medium carbon chain , 2003 .

[7]  Laura Cipolla,et al.  Combinatorial libraries of biocatalysts: application and screening. , 2004, Combinatorial chemistry & high throughput screening.

[8]  Chi‐Huey Wong,et al.  Synthesis of complex carbohydrates and glycoconjugates: enzyme-based and programmable one-pot strategies. , 2000, Chemical reviews.

[9]  M. Scigelová,et al.  Glycosidases—a great synthetic tool , 1999 .

[10]  E. Vulfson,et al.  Identification of novel polyphenol oxidase inhibitors by enzymatic one-pot synthesis and deconvolution of combinatorial libraries. , 2001, Biotechnology and bioengineering.

[11]  S. Roseman,et al.  Reflections on Glycobiology* 1 , 2001, The Journal of Biological Chemistry.

[12]  D. Clark,et al.  Combinatorial biocatalysis: a natural approach to drug discovery. , 1998, Trends in biotechnology.

[13]  J Thiem Applications of enzymes in synthetic carbohydrate chemistry. , 1995, FEMS microbiology reviews.

[14]  Y. Khmelnitsky,et al.  Biocatalytic combinatorial synthesis. , 1999, Bioorganic & medicinal chemistry.

[15]  A. Klibanov Why are enzymes less active in organic solvents than in water? , 1997, Trends in biotechnology.

[16]  B. G. Davis,et al.  Biocatalysis and enzymes in organic synthesis. , 2001, Natural product reports.

[17]  M. Ferrer,et al.  A Simple Procedure for the Regioselective Synthesis of Fatty Acid Esters of Maltose, Leucrose, Maltotriose and n-Dodecyl Maltosides , 2000 .

[18]  A. Varki,et al.  Biological roles of oligosaccharides: all of the theories are correct , 1993, Glycobiology.

[19]  Jian‐He Xu,et al.  Use of apple seed meal as a new source of β-glucosidase for enzymatic glucosylation of 4-substituted benzyl alcohols and tyrosol in monophasic aqueous-dioxane medium , 2004 .

[20]  J. Dordick,et al.  The evolution of biotransformation technologies. , 1998, Current opinion in microbiology.

[21]  B. Wilkinson,et al.  Biocatalysis in pharmaceutical preparation and alteration. , 2006, Current opinion in chemical biology.

[22]  S. Riva Biocatalytic modification of natural products. , 2001, Current opinion in chemical biology.

[23]  Huilei Yu,et al.  Identification, purification and characterization of β-glucosidase from apple seed as a novel catalyst for synthesis of O-glucosides , 2007 .

[24]  M. Himmel,et al.  The potential of cellulases and cellulosomes for cellulosic waste management. , 2007, Current opinion in biotechnology.

[25]  Sajja Hari Krishna,et al.  Developments and trends in enzyme catalysis in nonconventional media. , 2002, Biotechnology advances.

[26]  Chi‐Huey Wong,et al.  Enzymes in Organic Synthesis: Application to the Problems of Carbohydrate Recognition (Part 1) , 1995 .

[27]  L. Weber High-diversity combinatorial libraries. , 2000, Current opinion in chemical biology.

[28]  D. Crout,et al.  Glycosidases and glycosyl transferases in glycoside and oligosaccharide synthesis. , 1998, Current opinion in chemical biology.

[29]  D. Clark,et al.  Combinatorial biocatalysis: taking the lead from nature. , 1999, Current opinion in biotechnology.