Alkynyl polysaccharides: synthesis of propargyl potato starch followed by subsequent derivatizations

Tankam, Pascal F.; Müller, Romy; Mischnick, Petra; Hopf, Henning

doi:10.1016/j.carres.2007.05.017

Cited by 31 publications

(22 citation statements)

References 21 publications

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“…Positions of substitution could be deduced from shifted fragments by GLC/MS as has been elucidated for glucose derivates obtained from propargyl starch. [31,32] The mass spectra of glucose acetates of 2,4-di-O-propargyl derivates (i.e., 2,4-di-and 2,3,4-tri-O-Pg-glc) both are strongly dominated by m/z ¼ 149 (PgO¼CHÀ CH¼CHÀOPg) and could only be differentiated by m/z ¼ 136 (PgOÀCH¼CHÀOPg mainly formed from C2-C3) for the two 2,3,4-substituted diastereoisomers, and by very minor peaks at M-43 (CH 3 CO) and/or M-59 (CH 3 COO), from which the number of substituents can be deduced. Peak areas from GLC/FID analysis were corrected according to the ECR concept [41,42] for quantitative evaluation.…”

Section: Resultsmentioning

confidence: 99%

“…Peaks were assigned by gas chromatography/mass spectrometry (GCMS) analysis. For quantitative evaluation peak areas were corrected according to the ECR concept; [41,42] [31,32] …”

Section: Gas/liquid Chromatographymentioning

confidence: 99%

“…[26][27][28][29][30] We have demonstrated the potential of our concept of unsaturated polysaccharide ethers as reactive intermediates with propargyl starches and methyl-2,3-di-O-propargylglucosides as model compounds. [31,32] The terminal C C triple bond can undergo 1,3-dipolar cycloaddition with azides under mild conditions and at a wide range of functional group compatibility. [33][34][35][36][37][38] In an interesting approach, biodegradable microcapsules have been produced by 'clicking together' acetylenic and azido derivatives of dextrans.…”

Section: Introductionmentioning

confidence: 99%

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Alkynyl Ethers of Glucans: Substituent Distribution in Propargyl‐, Pentynyl‐ and Hexynyldextrans and ‐amyloses and Support for Silver Nanoparticle Formation

Tahir

Bork

Risberg

et al. 2010

Macro Chemistry & Physics

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Alkynyldextrans with a DS in the range 0.1–1.67 have been prepared as reactive intermediates for further polymer‐analogous functionalisation. DS and substituent distribution were determined by GLC and GLCMS after hydrolysis and acetylation, or methanolysis and trimethylsilylation. Reactivity was in the order O‐2 > O‐4 ≥ O‐3 with pronounced differences in the distinct patterns for propargyl ethers and its higher homologous. A large deviation from a random substituent distribution was observed. Propargyldextrans were not stable during long‐time storage in the solid state, while terminal pentynyl and hexynyl ethers are. Pentynyldextrans showed structure formation of various geometries. They bound silver efficiently, yielding silver nanoparticles by reduction.magnified image

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Section: Resultsmentioning

confidence: 99%

“…Peaks were assigned by gas chromatography/mass spectrometry (GCMS) analysis. For quantitative evaluation peak areas were corrected according to the ECR concept; [41,42] [31,32] …”

Section: Gas/liquid Chromatographymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Alkynyl Ethers of Glucans: Substituent Distribution in Propargyl‐, Pentynyl‐ and Hexynyldextrans and ‐amyloses and Support for Silver Nanoparticle Formation

Tahir

Bork

Risberg

et al. 2010

Macro Chemistry & Physics

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“…In this way, Hopf and co-workers described an etherification of potato starch using sodium hydroxide or Li dimsyl in dimethylsulfoxide, and propargyl bromide [49]. Thus, they established an order of reactivity, which was 2 > 6 >> 3.…”

Section: Positions 2 3 and 6 In Starchmentioning

confidence: 99%

Polysaccharides: The “Click” Chemistry Impact

et al. 2011

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Polysaccharides are complex but essential compounds utilized in many areas such as biomaterials, drug delivery, cosmetics, food chemistry or renewable energy. Modifications and functionalizations of such polymers are often necessary to achieve molecular structures of interest. In this area, the emergence of the "click" chemistry concept, and particularly the copper-catalyzed version of the Huisgen 1,3-dipolar cycloaddition reaction between terminal acetylenes and azides, had an impact on the polysaccharides chemistry. The present review summarizes the contribution of "click" chemistry in the world of polysaccharides.

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“…The copper-catalyzed azidealkyne cycloaddition (CuAAC) is one of the most used ''click''-reaction employed in polymer synthesis, offering extensive possibilities to tailor polymer properties Sachsenhofer 2007, 2008;Fournier et al 2007;Meldal 2008;Rostovtsev et al 2002;Tornoe et al 2002). Click-chemistry has also gained attention in the modification of polysaccharides and several articles on the topic can be found (Bernard et al 2008;De Geest et al 2008a, b;Hafrén et al 2006;Hasegawa et al 2006;Koschella et al 2010;Krouit et al 2008;Liebert et al 2006;Schatz et al 2009;Tankam et al 2007;Zhang et al 2009;Zhao et al 2010).…”

Section: Introductionmentioning

confidence: 99%

Surface functionalization of nanofibrillated cellulose using click-chemistry approach in aqueous media

et al. 2011

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In the present work, amino functionalized nanofibrillated cellulose (NFC) was prepared using click-chemistry in aqueous reaction conditions. First, reactive azide groups were introduced on the surface of NFC by the etherification of 1-azido-2,3-epoxypropane in alkaline water/isopropanol-mixture at ambient temperature. Then the azide groups were reacted with propargyl amine utilizing copper catalyzed azide-alkyne cycloaddition (CuAAC), leading to pH-responsive 1,2,3-triazole-4-methanamine decorated NFC. The reaction products were characterized using Fourier transform infrared spectroscopy, elemental analysis and X-ray photoelectron spectroscopy. The presence of the attached azide groups was also confirmed by reacting them with 5-(dimethylamino)-N-(2-propyl)-1-naphthalenesulfonamide by CuAAC, yielding highly fluorescent NFC. In addition, atom force microscopy and rheology studies confirmed that the original NFC nanostructure was maintained during the synthesis.

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Alkynyl polysaccharides: synthesis of propargyl potato starch followed by subsequent derivatizations

Cited by 31 publications

References 21 publications

Alkynyl Ethers of Glucans: Substituent Distribution in Propargyl‐, Pentynyl‐ and Hexynyldextrans and ‐amyloses and Support for Silver Nanoparticle Formation

Alkynyl Ethers of Glucans: Substituent Distribution in Propargyl‐, Pentynyl‐ and Hexynyldextrans and ‐amyloses and Support for Silver Nanoparticle Formation

Polysaccharides: The “Click” Chemistry Impact

Surface functionalization of nanofibrillated cellulose using click-chemistry approach in aqueous media

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