Fructose-permeable liquid membranes containing boronic acid carriers

被引:30
作者
Duggan, PJ [1 ]
机构
[1] Monash Univ, Sch Chem, Melbourne, Vic 3800, Australia
关键词
D O I
10.1071/CH03282
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Liquid membranes that contain boronic acids have potential application in environmentally benign industrial D-fructose production. This review describes our efforts to develop boronic acid carriers that promote high fluxes, that are resistant to leaching, and that are highly selective for fructose over other sugars. Considerable progress has been made with multidentate boronic acid carriers. Initial attempts to transport D-fructose as macrocyclic beta-D-fructopyranose diesters appeared to suffer from competitive transport of macrocyclic alpha-D-glucofuranose diesters, and did not lead to high D-fructose selectivity. On the other hand, carriers that can bind multiple equivalents of D-fructose as tridentate beta-D-fructofuranose esters have been much more effective. Unfortunately, D-fructose selectivity is still apparently limited by a competitive and boronic acid-independent non-selective 'mobile fixed site relay' transport process. However, further progress will be possible through improved carrier design, careful investigation of the various stages of the transport process, and the use of more industrially useful membrane configurations.
引用
收藏
页码:291 / 299
页数:9
相关论文
共 39 条
[1]   Cavitand boronic acids mediate highly selective fructose transport [J].
Altamore, TM ;
Barrett, ES ;
Duggan, PJ ;
Sherburn, MS ;
Szydzik, ML .
ORGANIC LETTERS, 2002, 4 (20) :3489-3491
[2]  
ALTAMORE TM, UNPUB
[3]   Complexation in pseudorotaxanes based on α-cyclodextrin and different α,ω-diaminoalkanes by NMR diffusion measurements [J].
Avram, L ;
Cohen, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (08) :2639-2644
[4]   Contribution to the theory of acid and basic catalysis. The mutarotation of glucose [J].
Bronsted, JN ;
Guggenheim, EA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1927, 49 :2554-2584
[5]   NMR diffusion coefficient study of steroid-cyclodextrin inclusion complexes [J].
Cameron, KS ;
Fielding, L .
MAGNETIC RESONANCE IN CHEMISTRY, 2002, 40 :S106-S109
[6]   MECHANISM IN CARBOHYDRATE CHEMISTRY [J].
CAPON, B .
CHEMICAL REVIEWS, 1969, 69 (04) :407-+
[7]  
COTE GL, 2000, 21 INT CARB S JUL CA
[8]   Separation of fructose from a mixture of sugars using supported liquid membranes [J].
Di Luccio, M ;
Smith, BD ;
Kida, T ;
Borges, CP ;
Alves, TLM .
JOURNAL OF MEMBRANE SCIENCE, 2000, 174 (02) :217-224
[9]   Highly selective lipophilic diboronic acid that transports fructose as the trisdentate 2,3,6-β-D-fructofuranose ester [J].
Draffin, SP ;
Duggan, PJ ;
Duggan, SAM ;
Norrild, JC .
TETRAHEDRON, 2003, 59 (46) :9075-9082
[10]   Highly fructose selective transport promoted by boronic acids based on a pentaerythritol core [J].
Draffin, SP ;
Duggan, PJ ;
Duggan, SAM .
ORGANIC LETTERS, 2001, 3 (06) :917-920