Targeted allylation and propargylation of galactose-containing polysaccharides in water

Carbohydrate Polymers

Volumn 100, Issue , 2014, Pages 46-54

  Leppänen, Ann Sofie ^a   Xu, Chunlin ^a,b,c   Parikka, Kirsti ^d   Eklund, Patrik ^a   Sjöholm, Rainer ^a   Brumer, Harry ^b,c   Tenkanen, Maija ^d   Willför, Stefan ^a  

^a ÅBO AKADEMI UNIVERSITY   (Finland)

^b ALBANOVA UNIVERSITY CENTER   (Sweden)

^c ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

^d UNIVERSITY OF HELSINKI   (Finland)

Author keywords

Allylation; Guar galactomannan; Indium mediated; MALDI TOF MS; Polysaccharides; Propargylation; Spruce galactoglucomannan; Tamarind xyloglucan

Indexed keywords

GALACTOGLUCOMANNAN; GUAR GALACTOMANNAN; MALDI TOF MS; PROPARGYLATION; XYLOGLUCANS;

ALDEHYDES; ALLYLATION; INDIUM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERS; INDUCTIVELY COUPLED PLASMA;

POLYSACCHARIDES;

CYAMOPSIS TETRAGONOLOBA; PICEA; TAMARINDUS INDICA;

ALKENE; DRUG DERIVATIVE; GALACTOSE; INDIUM; PARGYLINE; POLYSACCHARIDE; PROPARGYL BROMIDE; RAFFINOSE; WATER;

ALLYLATION; ARTICLE; CATALYSIS; CHEMISTRY; GUAR GALACTOMANNAN; INDIUM MEDIATED; MALDI-TOF-MS; OXIDATION REDUCTION REACTION; PROPARGYLATION; SPRUCE GALACTOGLUCOMANNAN; TAMARIND XYLOGLUCAN;

ALLYLATION; GUAR GALACTOMANNAN; INDIUM MEDIATED; MALDI-TOF-MS; POLYSACCHARIDES; PROPARGYLATION; SPRUCE GALACTOGLUCOMANNAN; TAMARIND XYLOGLUCAN;

ALKENES; CATALYSIS; GALACTOSE; INDIUM; OXIDATION-REDUCTION; PARGYLINE; POLYSACCHARIDES; RAFFINOSE; WATER;

EID: 84887471490     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2012.11.053     Document Type: Article

References (40)

1. D. Ameye, J. Voorspoels, P. Foreman, P. Richardson, S. Geresh, and J.P. Remon Ex vivo bioadhesion and in vivo testosterone bioavailability study of different bioadhesive formulations based on starch-g-poly(acrylic acids) copolymers and starch/poly(acrylic acids) mixtures Journal of Controlled Release 79 2002 173 182 (Pubitemid 34164171)
2. E. Balla, A. Zamyatina, A. Hofinger, and P. Kosma Synthesis of a deoxy analogue of ADP l-glycero-d-manno-heptose Carbohydrate Research 342 2007 2537 2545 (Pubitemid 47633515)
3. S.P. Bhuniya, S. Rahman Md, A.J. Satyanand, M.M. Gharia, and A.M. Dave Novel route to synthesis of allyl starch and biodegradable hydrogel by copolymerizing allyl-modified starch with methacrylic acid and acrylamide Journal of Polymer Science, Part A: Polymer Chemistry 41 2003 1650 1658 (Pubitemid 36602242)
4. C.M. Cheng, A.W. Martinez, J.L. Gong, C.R. Mace, S.T. Phillips, and E. Carrilho Paper-based ELISA Angewandte Chemie-International Edition 49 2010 4771 4774
5. T.-H. Chan, and C.-J. Li A concise chemical sunthesis of (+)-3-deoxy-d-glycero-d-galacto-nonulosonic acid (KDN) Journal of the Chemical Society, Chemical Communications 1992 747 748
6. A.G. Cunha, and A. Gandini Turning polysaccharides into hydrophobic materials: A critical review. Part 1. Cellulose Cellulose 17 2010 875 889
7. A.G. Cunha, and A. Gandini Turning polysaccharides into hydrophobic materials: A critical review. Part 2. Hemicelluloses, chitin/chitosan, starch, pectin and alginates Cellulose 17 2010 1045 1065
8. J. Duanmu, E.K. Gamstedt, and A. Rosling Synthesis and preparation of crosslinked allylglycidyl ether-modified starch-wood fibre composites Starch Stärke 59 2007 523 532 (Pubitemid 350171723)
9. P.-E. Elchinger, P.-A. Faugeras, B. Boëns, F. Brouillitte, D. Montplaisir, and R. Zerrouki Polysaccharides: The click chemistry impact Polymers 3 2011 1607 1651
10. J. Gao, V. Martichonok, and G.M. Whitesides Synthesis of a phosphonate analog of sialic acid (Neu5Ac) using indium-mediated allylation of unprotected carbohydrates in aqueous media Journal of Organic Chemistry 61 1996 9538 9540 (Pubitemid 127562819)
11. D.M. Gordon, and G.M. Whitesides Indium-mediated allylations of unprotected carbohydrates in aqueous media: a short synthesis of sialic acid Journal of Organic Chemistry 58 1993 7937 7938 (Pubitemid 24065057)
12. S. Hartmans, H.T. de Vries, P. Beijer, R.L. Brady, M. Hofbauer, and A.J. Haandrikman Production of oxidized galactomannan and its applications in the paper industry P. Gatenholm, M. Tenkanen, Hemicelluloses: Science and technology 2004 American Chemical Society Washington, DC 360 371
13. T. Heinze, T. Lincke, D. Fenn, and A. Koschella Efficient allylation of cellulose in dimethyl sulfoxide/tetrabutylammonium fluoride trihydrate Polymer Bulletin 61 2008 1 9
14. A.M.L. Huijbrechts, J. Huang, H.A. Schols, B. van Lagen, G.M. Visser, and C. Boeriu 1-Allyloxy-2-hydroxy-propyl-starch: Synthesis and characterization Journal of Polymer Science Part A: Polymer Chemistry 45 2007 2734 2744 (Pubitemid 47146856)
15. A.M.L. Huijbrechts, R. ter Haar, H.A. Schols, M.C.R. Franssen, C.G. Boeriu, and E.J.R. Sudhölter Synthesis and application of epoxy starch derivatives Carbohydrate Polymers 79 2010 858 866
16. M.B. Isaac, and T.-K. Chan Indium-mediated coupling of aldehydes with prop-2-ynyl bromides in aqueous media Chemical Communications 10 1995 1003 1004
17. E. Kim, D.M. Gordon, W. Schmid, and G.M. Whitesides Tin- and indium-mediated allylation in aqueous media: Application to unprotected carbohydrates Journal of Organic Chemistry 58 1993 5500 5507
18. A.-S. Leppänen, O. Niittymäki, K. Parikka, M. Tenkanen, P. Eklund, and R. Sjöholm Metal-mediated allylation of enzymatically oxidized methyl α-d-galactopyranoside Carbohydrate Research 345 2010 2610 2615
19. C.-J. Li Aqueous Barbier-Grignard type reaction: Scope, mechanism, and synthetic applications Tetrahedron 52 1996 5643 5668 (Pubitemid 26113048)
20. M.S. Lin, and C.S. Huang Syntheses and characterizations of allyl cellulose and glycidyl cellulose Journal of Polymer Science, Part A: Polymer Chemistry 30 1992 2303 2312
21. P. Maharjan, B.W. Woonton, L.E. Bennett, G.W. Smithers, K. DeSilva, and M.T.W. Hearn Novel chromatographic separation - The potential of smart polymers Innovative Food Science and Emerging Technologies 9 2008 232 242 (Pubitemid 351215970)
22. Z. Pakulski, and A. Zamojski Diastereoselective propargylation of sugar aldehydes. New synthesis of 6-deoxyheptoses Tetrahedron 53 1997 2653 2666 (Pubitemid 27078201)
23. C.S. Paulsen, and R. Madsen Carbohydrate Carbocyclization by a zinc-mediated tandem reaction and ring-closing enyne metathesis Journal of Organic Chemistry 67 2002 4441 4449 (Pubitemid 34700800)
24. K. Parikka, and M. Tenkanen Oxidation of methyl α-d- galactopyranoside by galactose oxidase: Products formed and optimization of reaction conditions for production of aldehyde Carbohydrate Research 344 2009 14 20
25. K. Parikka, A.-S. Leppänen, L. Pitkänen, M. Reunanen, S. Willför, and M. Tenkanen Oxidation of polysaccharides by galactose oxidase Journal of Agricultural and food Chemistry 58 2010 262 271
26. K. Parikka, A.-S. Leppänen, C. Xu, L. Pitkänen, P. Eronen, and M. Österberg Functional and anionic cellulose-interacting polymers by selective chemo-enzymatic carboxylation of galactose-containing polysaccharides Biomacromolecules 13 2012 2418 2428
27. C. Pétrier, and J.-L. Luche Allylzinc reagent additions in aqueous media Journal of Organic Chemistry 50 1985 910 912
28. W. Schmid, and G.M. Whitesides Carbon-carbon bond formation in aqueous ethanol: Diastereoselective transformation of unprotected carbohydrates to higher carbon sugar using allyl bromide and tin metal Journal of American Chemical Society 113 1991 6674 6675
29. O. Spadiut, L. Olsson, and H. Brumer A comparative summary of expression systems for the recombinant production of galactose oxidase Microbial Cell Factories 9 2010 68
30. P.F. Tankam, R. Müller, P. Mischnick, and H. Hopf Alkynyl polysaccharides: Synthesis of propargyl potato starch followed by subsequent derivatizations Carbohydrate Research 342 2007 2049 2060 (Pubitemid 47135602)
31. C.G. Tomecko, and R. Adams The allylation of various carbohydrates Journal of the American Chemical Society 45 1923 2698 2701
32. J.W. Whittaker Free radical catalysis by galactose oxidase Chemical Reviews 103 2003 2347 2363
33. W.C. Wielinga Galactomannans G.O. Philips, P.A. Williams, Handbook of hydrocolloids 2000 Woodhead Publishing Ltd. Cambridge 137 154
34. S. Willför, P. Rehn, A. Sundberg, K. Sundberg, and B. Holmbom Recovery of water-soluble acetylgalactoglucomannans from mechanical pulp of spruce Tappi Journal 2 2003 27 32
35. S. Willför, R. Sjöholm, C. Laine, M. Roslund, J. Hemming, and B. Holmbom Characterization of water-soluble galactoglucomannans from Norway spruce wood and thermomechanical pulp Carbohydrate Polymers 52 2003 175 187
36. S. Willför, A. Pranovich, T. Tamminen, J. Puls, C. Laine, and A. Suurnäkki Carbohydrate analysis of plant materials with uronic acid-containing polysaccharides - A comparision between different hydrolysis and subsequent chromatographic analytical techniques Industrial Crops and Products 29 2009 571 580
37. C. Xu, A.-S. Leppänen, P. Eklund, P. Holmlund, R. Sjöholm, and K. Sundberg Acetylation and characterization of spruce (Picea abies) galactoglucomannans Carbohydrate Research 345 2010 810 816
38. C. Xu, C. Eckerman, A. Smeds, M. Reunanen, P.C. Eklund, and R. Sjöholm Carboxymethylated spruce galactoglucomannans: Preparation, characterisation, dispersion stability, water-in-oil emulsion stability, and sorption on cellulose surface Nordic Pulp and Paper Research Journal 26 2011 167 178
39. C. Xu, O. Spadiut, A.C. Araújo, A. Nakhai, and H. Brumer Chemo-enzymatic assembly of clickable cellulose surfaces via multivalent polysaccharides ChemSusChem 5 2012 661 665
40. W.S. York, L.K. Harvey, R. Guillen, P. Albersheim, and A.G. Darvill The structure of plant cell walls. XXXVI. Structural analysis of tamarind seed xyloglucan oligosaccharides using beta galactosidase digestion and spectroscopic methods Carbohydrate Research 248 1993 285 301 (Pubitemid 23302986)