Structural characterization by 13C-NMR spectroscopy of products synthesized in vitro by polysaccharide synthases using 13C-enriched glycosyl donors: Application to a UDP-glucose:(1→3)β-D-glucan synthase from blackberry (Rubus fruticosus)

Glycobiology

Volumn 14, Issue 9, 2004, Pages 775-781

  Fairweather, Jon K ^b   Him, Joséphine Lai Kee ^b   Heux, Laurent ^b   Driguez, Hugues ^b   Bulone, Vincent ^a  

^a UNIVERSITÉ LYON 1   (France)

^b CENTRE DE RECHERCHES SUR LES MACROMOLÉCULES VÉGÉTALES CERMAV CNRS   (France)

Author keywords

13C NMR spectroscopy; In vitro synthesis of (1 3) D glucan; Polysaccharide synthases; Structural analysis of polysaccharides; UDP U13C glocuse

Indexed keywords

1,3 BETA GLUCAN SYNTHASE; CARBON 13; GLUCAN; GLYCAN; GLYCOSIDASE; GLYCOSYLTRANSFERASE; NUCLEOTIDE; POLYMER; POLYSACCHARIDE; RADIOACTIVE MATERIAL; SUGAR; URIDINE DIPHOSPHATE GLUCOSE;

ARTICLE; BLACKBERRY; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CELL MEMBRANE; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENZYME SUBSTRATE; IN VITRO STUDY; LIQUID; PRIORITY JOURNAL; PROTEIN HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; SENSITIVITY ANALYSIS; SOLID STATE; STRUCTURE ANALYSIS; SYNTHESIS; VALIDATION PROCESS;

CARBON RADIOISOTOPES; GLUCOSYLTRANSFERASES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; ROSACEAE; URIDINE DIPHOSPHATE GLUCOSE;

RUBUS; RUBUS FRUTICOSUS;

EID: 4444339341     PISSN: 09596658     EISSN: None     Source Type: Journal    
DOI: 10.1093/glycob/cwh097     Document Type: Article

References (39)

1. Atalla, R.H. (1999) Celluloses. In M.B. Pinto (Ed.), Comprehensive natural products chemistry, vol. 3. Elsevier, Amsterdam, pp. 529-598.
2. Atalla, R.H. and VanderHart, D.L. (1984) Native cellulose: a composite of two distinct crystalline forms. Science, 223, 283-285.
3. Barber, G.A. and Behrman, E.J. (1991) The synthesis and characterization of uridine 5′-(β-L-rhamnopyranosyl diphosphate) and its role in the enzymic synthesis of rutin. Arch. Biochem. Biophys., 288, 239-242.
4. 14C]galacturonic acid. Anal. Biochem., 280, 173-177.
5. Bulone, V., Fincher, G.B., and Stone, B.A. (1995) In vitro synthesis of a microfibrillar (1→3)-β-glucan by a ryegrass (Lolium multiflorum) endosperm (1→3)-β-glucan synthase enriched by product entrapment. Plant. J., 8, 213-225.
6. Chuah, C.T. and Sarko, A. (1983) Triple-helical crystalline structure of curdlan and paramylon hydrates. Macromolecules, 16, 1375-1382.
7. Colombani, A., Djerbi, S., Bessueille, L., Blomqvist, K., Ohlsson, A., Berglund, T., Teeri, T.T., and Bulone, V. (Forthcoming) In vitro synthesis of (1→3)-β-D-glucan (callose) and cellulose by detergent extracts of membranes from cell suspension cultures of hybrid aspen. Cellulose.
8. Cui, W., Wood, P.J., Blackwell, B., and Nikiforuk, J. (2000) Physicochemical properties and structural characterization by two-dimensional NMR spectroscopy of wheat β-D-glucan-comparison with other cereal β-D-glucans. Carbohydr. Polym., 41, 249-258.
9. 13C-N.M.R. spectroscopy of β-D-glucans, amylopectin, and glycogen. Carbohydr. Res., 100, 103-116.
10. Delmer, D.P. (1999) Cellulose biosynthesis: exciting times for a difficult field of study. Annu. Rev. Plant Physiol. Plant Mol. Biol., 50, 245-276.
11. Engelhardt, J. (1995) Sources, industrial derivatives and commercial application of cellulose. Carbohydr. Eur., 12, 5-14.
12. 13C-N.M.R. spectra of the xylo- and cello-oligosaccharides. Carbohydr. Res., 84, 137-146.
13. Gay, L., Chanzy, H., Bulone, V., Girard, V., and Fèvre, M. (1993) In vitro synthesis of crystalline chitin by a solubilised enzyme from the cellulosic fungus Saprolegnia monoïca. J. Gen. Microbiol., 139, 2117-2122.
14. Gibeaut, D.M. and Carpita, N.C. (1993) Synthesis of (1→3, 1→4)-β-D-glucan in the Golgi apparatus of maize coleoptiles. Proc. Natl Acad. Sci. USA, 90, 3850-3854.
15. Hanessian, S., Lu, P.-P., and Ishida, H. (1998) One-step, stereocontrolled synthesis of glycosyl 1-phosphates, uridine-5′-diphosphogalactose, and uridine-5′ -diphosphoglucose from unprotected glycosyl donors. J. Am. Chem. Soc., 120, 13296-13300.
16. 13C CP-MAS NMR. Carbohydr. Polym., 40, 115-124.
17. Heux, L., Brugnerotto, J., Desbrières, J., Versali, M.F., and Rinaudo, M. (2000) Solid state NMR for determination of degree of acetylation of chitin and chitosan. Biomacromolecules, 1, 746-751.
18. Kerry, M.E., Gregory, A.C.E., and Bolwell, G.P. (2001) Differential behaviour of four plant polysaccharide synthases in the presence of organic solvents. Phytochemistry, 57, 1055-1060.
19. Kogan, G., Alföldi, J., and Masler, L. (1988) Carbon-13 NMR spectroscopic investigation of two yeast cell wall β-D-glucans. Biopolymers, 27, 1055-1063.
20. Kudlicka, K. and Brown, R.M. Jr. (1997) Cellulose and callose biosynthesis in higher plants. I. Solubilization and separation of (1→3)- and (1→4)-β-glucan synthase activities from mung bean. Plant Physiol., 115, 643-656.
21. Kudlicka, K., Brown, R.M. Jr, Li, L., Lee, J.H., Shin, H., and Kuga, S. (1995) β-Glucan synthesis in the cotton fiber. IV. In vitro assembly of the cellulose I allomorph. Plant Physiol., 107, 111-123.
22. Kudlicka, K., Lee, J.H., and Brown, R.M. Jr. (1996) A comparative analysis of in vitro cellulose synthesis from cell-free extracts of mung bean (Vigna radiata, Fabaceae) and cotton (Gossypium hirsutum, Malvaceae). Am. J. Bot., 83, 274-284.
23. Lai Kee Him, J., Pelosi, L., Chanzy, H., Putaux, J.-L., and Bulone, V. (2001) Biosynthesis of (1→3)-β-D-glucan (callose) by detergent extracts of a microsomal fraction from Arabidopsis thaliana. Eur. J. Biochem., 268, 4628-4638.
24. Lai Kee Him, J., Chanzy, H., Müller, M., Putaux, J.-L., Imai, T., and Bulone, V. (2002) In vitro versus in vivo cellulose microfibrils from plant primary wall synthases: structural differences. J. Biol. Chem., 277, 36931-36939.
25. Lai Kee Him, J., Chanzy, H., Pelosi, L., Putaux, J.-L., and Bulone, V. (2003) Recent developments in the field of in vitro biosynthesis of plant β-glucans. In R.A. Gross, and H.N. Cheng (Eds.), Biocatalysis in polymer science. ACS Symp. Series no. 840, American Chemical Society, Washington, pp. 65-77.
26. β in lignocellulosic materials. Carbohydr. Res., 261, 119-131.
27. Meikle, P.J., Ng, K., Johnson, E., Hoogenraad, N.J., and Stone, B.A. (1991) The β-glucan synthase from Lolium multiflorum: detergent solubilization, purification using monoclonal antibodies, and photo-affinity labelling with a novel photoreactive pyrimidine analogue of uridine 5′-diphosphoglucose. J. Biol. Chem., 266, 22569-22581.
28. 13C CP/MAS NMR spectroscopy and AFM study of the structure of Glucagel™, a gelling β-glucan from barley. Carbohydr. Res., 315, 169-179.
29. Peersen, O.B., Wu, X.L., Kustanovich, I., and Smith, S.O. (1993) Variable-amplitude cross-polarization MAS NMR. J. Magn. Reson. Ser. A, 104, 334-339.
30. Pelosi, L., Imai, T., Chanzy, H., Heux, L., Buhler, E., and Bulone, V. (2003) Structural and morphological diversity of (1→3)-β-D-glucans synthesized in vitro by enzymes from Saprolegnia monoïca. Comparison with a corresponding in vitro product from blackberry (Rubus fruticosus). Biochemistry, 42, 6264-6274.
31. 14C]acetate. Anal. Biochem., 91, 490-495.
32. Ruiz-Herrera, J. and Bartnicki-Garcia, S. (1974) Synthesis of cell wall microfibrils in vitro by a "soluble" chitin synthetase from Mucor rouxii. Science, 186, 357-359.
33. Ruiz-Herrera, J., Sing, V.O., Van der Woude, W.J., and Bartnicki-Garcia, S. (1975) Microfibril assembly by granules of chitin synthetase. Proc. Natl Acad. Sci. USA, 72, 2706-2710.
34. Sabesan, S. and Neira, S. (1992) Synthesis of glycosyl phosphates and azides. Carbohydr. Res., 223, 169-185.
35. 13C-nuclear magnetic resonance study of polysaccharide gels. Molecular architecture in the gels consisting of fungal, branched (1→3)-β-D-glucans (lentinan and schizophyllan) as manifested by conformational changes induced by sodium hydroxide. Carbohydr. Res., 74, 227-240.
36. Saito, H., Yokoi, M., and Yoshioka, Y. (1989) Effect of hydration on conformational change or stabilization of (1→3)-β-D-glucans of various chain lengths in the solid state as studied by high-resolution solid-state carbon-13 NMR spectroscopy. Macromolecules, 22, 3892-3898.
37. 1H-Tetrazole as catalyst in phosphomorpholidate coupling reactions: efficient synthesis of GDP-fucose, GDP-mannose, and UDP-galactose. J. Org. Chem., 62, 2144-2147.
38. Wong, C.-H. and Whitesides, G.M. (1994) Enzymes in synthetic organic chemistry. Tetrahedron Organic Chemistry Series, vol. 12. Pergamon, Oxford, pp. 256-264.
39. Zhang, Q. and Liu, H.-W. (2001) Chemical synthesis of UDP-β-L-arabinofuranose and its turnover to UDP-β -L-arabinopyranose by UDP-galactopyranose mutase. Bioorg. Med. Chem. Lett., 11, 145-149.