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Savage, Tammy; Mitchell, John; Trivedi, Vivek; Wicks, Stephen; Waters, Laura J. (2015)
Publisher: Elsevier
Languages: English
Types: Article
Subjects: QD

Classified by OpenAIRE into

mesheuropmc: technology, industry, and agriculture, polycyclic compounds, carbohydrates (lipids), lipids (amino acids, peptides, and proteins)
Batch synthesis of sulphobutyl ether β-cyclodextrin (also known as SBE-β-CD or SBECD) is a process effectively divided into three main stages, i.e. initial reagent dissolution, a sulphoalkylation reaction and final reaction quenching. This reaction is followed by downstream processing and purification, and ultimate isolation of the solid SBECD material. However, a feature associated with using this synthetic method is that a high proportion of lower substituted SBECD is observed. There is therefore a need to provide an improved synthetic method for producing higher substituted cyclodextrins.\ud \ud The authors here present a Continuous Tank Reactor (CTR) method for preparing sulphobutyl ether-cyclodextrins. The method comprises first contacting cyclodextrin with a base to form activated cyclodextrin. The method then involves separately contacting the activated cyclodextrin with an 1,4-butane sultone to form sulphoalkyl ether-cyclodextrin.\ud \ud The activation reaction is carried out in batch synthesis mode and the sulphoalkylation reaction is carried out under continuous flow conditions resulting in a novel method for the synthesis of highly derivatised cyclodextrins.\ud \ud The work is particularly concerned with producing controlled substitution in sulphobutyl ether β-cyclodextrins and novel compositions of highly substituted sulphoalkyl ether β-cyclodextrins are described.
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    • 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 75 76 77 78 79 80 81 82 83 84 85 94 95 96 97 98 99 100 101 123 124 125 126 127 128 129 130 131 132 133 153 154 155 156 157 158 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 174 175 176 177 178 179 180 1. Shah, B.K., Sklavounos, C., 2000, Process for Making a Cyclodextrin. U.S.
    • 2. (a) Antle, V., 2009, Sulfoalkyl Ether Cyclodextrin Compositions. US Patent (b)Matos , J. R., Antle V. D. , 2013, A method of producing cyclodextrin 3. Tongiani, S., Vander Velde, D., Ozeki, T., Stella, V.J., Sulfoalkyl ether-alkyl ether cyclodextrin derivatives, their synthesis, NMR characterization, and binding of 6α-methylprednisolone, 2005, Journal of Pharmaceutical Sciences, V 94, Issue 11, 2380-2392.
    • 4. Rong D, D'Souza VT., 1990,A convinient method for functionalization of the 1993. An AM1 molecular orbital study of a-D-glucose and B-maltose: 6. Jindrich J, Pitha J, Lindberg B, Seffers P, Harata K. 1995, Regioselectivity of 8. Szeman, J. , Csabai, K. , Kekesi, K. , Szente, L. , Varga, G. , 2006, Novel 9. Szeman, J. , Sohajda, T. , Olah, E. , Varga, E. , Csabai, K. , Varga, G. , Grard S, Elfakir C, Dreux M., 2001, Analysis of sulfobutyl ether-betacyclodextrin mixtures by ion-spray mass spectrometry and liquid chromatography-ion-spray mass spectrometry.
    • J Chromatogr A., 3;925(1-2):79-87.
    • Stella, V. J. , Rajewski, R., 1994, Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use there of US 5,376,645, US 5376645 A Savage, T., Wicks, S ., Mitchell, J ., 2014, Patent CYCLODEXTRIN 20150025023, US Patent App. 14/333,417.
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