Biocatalytic Production, Preparation and Characterization of Large-ring Cyclodextrins

Cyclodextrins (CD) are cyclic oligosaccharides composed of six to more than sixty glucose units. Large-ring cyclodextrins (LR-CD) are novel CD comprised of more than eight glucose units with cavity structures and sizes different from that of commercially available CD<sub>6</sub> – CD<...

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Bibliographic Details
Main Author: Mokhtar, Mohd Noriznan
Other Authors: TU Chemnitz, Fakultät für Maschinenbau
Format: Doctoral Thesis
Language:English
Published: Universitätsbibliothek Chemnitz 2009
Subjects:
Online Access:http://nbn-resolving.de/urn:nbn:de:bsz:ch1-200900431
http://nbn-resolving.de/urn:nbn:de:bsz:ch1-200900431
http://www.qucosa.de/fileadmin/data/qucosa/documents/5765/data/Thesis.pdf
http://www.qucosa.de/fileadmin/data/qucosa/documents/5765/20090043.txt
Description
Summary:Cyclodextrins (CD) are cyclic oligosaccharides composed of six to more than sixty glucose units. Large-ring cyclodextrins (LR-CD) are novel CD comprised of more than eight glucose units with cavity structures and sizes different from that of commercially available CD<sub>6</sub> – CD<sub>8</sub>. LR-CD may offer unique molecular recognition properties and can be produced biocatalytically from starch using cyclodextrin glucanotransferase (CGTase, E.C. 2.4.1.19) in a short reaction time. LR-CD were isolated from glucose, CD<sub>6</sub> – CD<sub>8</sub> and other compounds by complexation of CD<sub>6</sub> – CD<sub>8</sub> as well as precipitation techniques. The yield of LR-CD (degree of polymerization from 9 to 21) was optimized using central composite design. Addition of polar organic solvents to the synthesis resulted in higher yields of LR-CD. LR-CD composed of 9 to 21 glucose units were successfully separated using reversed-phase of ODS-AQ chromatography and normal-phase of polyamine II chromatography. Maintaining optimized reaction conditions aided in a high yield of CD<sub>9</sub>; it could be separated with reasonable yield using a single step of polyamine II chromatography. A co-grinding method helped to obtain higher solubilization levels of glibenclamide, vitamin A acetate and vitamin D<sub>3</sub> in CD<sub>13</sub>, CD<sub>10</sub> and CD<sub>11</sub>, respectively when compared to other CD. Vitamin K<sub>1</sub> was solubilized in distilled water with CD<sub>6</sub> – CD<sub>13</sub> using a co-precipitation method. When compared with other CD, CD<sub>9</sub> was seen to be the best solubilizer. The analysis of complexes using ESI MS showed spironolactone and glibenclamide complexed with CD<sub>9</sub> and CD<sub>13</sub>, respectively.