Microflow synthesis of saccharide nucleoside diphosphate with cross-coupling reactions of monophosphate components

Chemical Engineering Journal

Volumn 198-199, Issue , 2012, Pages 33-37

  Chen, Kuan Hung ^a   Fang, Wei Feng ^a   Chen, Yu Tzu ^a   Fang, Jim Min ^a   Yang, Jing Tang ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

Microflow synthesis; Microreactors; Saccharide nucleoside diphosphate; Split and recombination (SAR)

Indexed keywords

BIOACTIVE COMPOUNDS; CROSS COUPLING REACTIONS; DIPHOSPHATES; HPLC ANALYSIS; MATERIAL INTERFACES; MICRO REACTOR; MICRO-FLOW; MONOPHOSPHATES; ORGANIC SYNTHESIS; SPLIT-AND-RECOMBINATION (SAR);

BATCH REACTORS; INTERFACES (MATERIALS); SYNTHESIS (CHEMICAL);

BIOMOLECULES;

EID: 84864304889     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2012.05.061     Document Type: Article

References (28)

1. Watkins W.M. Glycosyltransferases, early history, development and future prospects. Carbohydr. Res. 1986, 149:1-12.
2. Halliday J., Mckeveney D., Muldoon C., Rajaratnam P., Meutermans W. Targeting the forgotten transglycosylases. Biochem. Pharmacol. 2006, 71:957-967.
3. Stolz F., Blume A., Hinderlich S., Reutter W., Schmidt R.R. C-Glycosidic UDP-GlcNAc Analogues as Inhibitors of UDP-GlcNAc 2-epimerase. J. Org. Chem. 2004, 3304-3312.
4. Uchiyama T., Hindsgaul O. Rapid conversion of unprotected galactose analogs to their Udp-Derivatives for use in the chemo-enzymatic synthesis of unnatural oligosaccharides. J. Carbohydr. Chem. 1998, 17:1181-1190.
5. Liu C.Y., Guo C.W., Chang Y.F., Wang J.T., Shih H.W., Hsu Y.F., Chen C.W., Chen S.K., Wang Y.C., Cheng T.J.R., Ma C., Wong C.H., Fang J.M., Cheng W.C. Synthesis and evaluation of a new fluorescent transglycosylase substrate: lipid II-based molecule possessing a dansyl-C20 polyprenyl moiety. Org. Lett. 2010, 12:1608-1611.
6. VanNieuwenhze M.S., Mauldin S.C., Zia-Ebrahimi M., Winger B.E., Hornback W.J., Saha S.L., Aikins J.A., Blaszczak L.C. The first total synthesis of lipid II: the final monomeric intermediate in bacterial cell wall biosynthesis. J. Am. Chem. Soc. 2002, 124:3656-3660.
7. Marlow A.L., Kiessling L.L. Improved chemical synthesis of UDP-galactofuranose. Org. Lett. 2001, 3:2517-2519.
8. Timmons S.C., Jakeman D.L. Stereospecific synthesis of sugar-1-phosphates and their conversion to sugar nucleotides. Carbohydr. Res. 2008, 343:865-874.
9. Lin T.C., Fang J.M. Diphosphate formation using cyanuric chloride or triisopropylbenzenesulfonyl chloride as the activating agents. Tetrahedron Lett. 2011, 52:2232-2234.
10. 1. J. Am. Chem. Soc. 1961, 83:649-658.
11. Wittmann V., Wong C.H. 1H-tetrazole as catalyst in phosphomorpholidate coupling reactions: efficient synthesis of GDP-fucose, GDP-mannose, and UDP-galactose. J. Org. Chem. 1997, 62:2144-2147.
12. Yi C., Li C.W., Ji S., Yang M. Microfluidics technology for manipulation and analysis of biological cells. Anal. Chim. Acta 2006, 560:1-23.
13. Valera F.E., Quaranta M., Moran A., Blacker J., Armstrong A., Cabral J.T., Blackmond D.G. The flow's the thing...or is it? Assessing the merits of homogeneous reactions in flask and flow. Angew. Chem. Int. Ed. 2010, 49:2478-2485.
14. Hessel V., Hardt S., Löwe H. Chemical Micro Process Engineering: Fundamentals, Modelling and Reactions 2004, Wiley-VCH, Weinheim, Germany.
15. Génot V., Desportes S., Croushore C., Lefèvre J.P., Pansu R.B., Delaire J.A., von Rohr P.R. Synthesis of organic nanoparticles in a 3D flow focusing microreactor. Chem. Eng. J. 2010, 161:234-239.
16. Chen Y.T., Chen K.H., Fang W.F., Tsai S.H., Fang J.M., Yang J.T. Flash synthesis of carbohydrate derivatives in chaotic microreactors. Chem. Eng. J. 2011, 174:421-424.
17. Fang W.F., Yang J.T. A novel microreactor with 3D rotating flow to boost fluid reaction and mixing of viscous fluids. Sens. Actuators B 2009, 140:629-642.
18. Hsu M.H., Fang W.F., Lai Y.H., Yang J.T., Tsai T.L., Shieh D.B. Enhanced mobile hybridization of gold nanoparticles decorated with oligonucleotide in microchannel devices. Lab Chip 2010, 10:2583-2587.
19. Nguyen N.T., Wu Z. Micromixers-a review. J. Micromech. Microeng. 2005, 15:R1-R16.
20. Schwesinger N., Frank T., Wurmus H. A modular microfluid system with an integrated micromixer. J. Micromech. Microeng. 1996, 6:99-102.
21. Schönfeld F., Hessel V., Hofmann C. An optimized split-and-recombine micro-mixer with uniform 'chaotic' mixing. Lab Chip 2004, 4:65-69.
22. Lee J.N., Park C., Whitesides G.M. Solvent compatibility of poly(dimethylsiloxane)-based microfluidic devices. Anal. Chem. 2003, 75:6544-6554.
23. Hinderlich S., Stäsche R., Zeitler R., Reutter W.J. A bifunctional enzyme catalyzes the first two steps in N-acetylneuraminic acid biosynthesis of rat liver: purification and characterization of UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase. J. Biol. Chem. 1997, 272:24313-24318.
24. Montoya-Peleaz P.J., Riley J.G., Szarek W.A., Valvano M.A., Schutzbach J.S., Brockhausen I. Identification of a UDP-Gal: GlcNAc-R galactosyltransferase activity in Escherichia coli VW187. Bioorg. Med. Chem. Lett. 2005, 15:1205-1211.
25. Ginsberg C., Zhang Y.H., Yuan Y., Walker S. In vitro reconstitution of two essential steps in wall teichoic acid biosynthesis. ACS Chem. Biol. 2006, 1:25-28.
26. Blume A., Chen H., Reutter W., Schmidt R.R., Hinderlich S. 2',3'-Dialdehydo-UDP-N-acetylglucosamine inhibits UDP-N-acetylglucosamine 2-epimerase, the key enzyme of sialic acid biosynthesis. FEBS Lett. 2002, 521:127-132.
27. Stäsche R., Hinderlich S., Weise C., Effertz K., Lucka L., Moormann P., Reutter W.J.J. A bifunctional enzyme catalyzes the first two steps in N-acetylneuraminic acid biosynthesis of rat liver: molecular cloning and functional expression of UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase. J. Biol. Chem. 1997, 272:24319-24324.
28. (1). Further studies on aromatic phosphoramidates as a protecting group for phosphomonoesters. Nucleic Acid Res. 1974, 1:223-234.