Synthesis of branched cyclodextrins using activated carbon as a catalyst

被引:0
作者
Ishikura, Kandai [1 ]
Yanagihara, Kazunori [1 ]
Takagi, Hiroki [1 ]
机构
[1] Nihon Shokuhin Kako Co Ltd, 30 Tajima, Fuji, Shizuoka 4178530, Japan
关键词
Activated carbon; Branched cyclodextrins; Catalyst; Solubility; Inclusion complex; Hemolytic activity; HETEROBRANCHED BETA-CYCLODEXTRINS; SIDE-CHAINS; ENZYMATIC-SYNTHESIS; INCLUSION BEHAVIOR; NMR-SPECTROSCOPY; REVERSE ACTION; CYCLOMALTOOLIGOSACCHARIDES; MALTOTRIOSE; PULLULANASE; DRUGS;
D O I
10.1007/s10847-021-01089-z
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Activated carbon has been reported to act as a catalyst for condensation reactions between glucose molecules. The present study describes the use of activated carbon as a new catalyst for the synthesis of branched cyclodextrins (CDs). Two main methods have been used to synthesize branched CDs: a method using an enzymatic condensation or transfer reaction, and a method using a chemical reaction. However, these methods have problems such as a limited number of the types of branched CDs that can be synthesized that depend on the characteristics of the enzyme, the long reaction time required (several days or more), difficulty in synthesizing branched CD with a high degree of substitution (DS), the need for large quantities of environmentally harmful solvents, and a complicated and costly reaction. Using activated carbon as a catalyst, branched CDs with a high DS could be synthesized within a relatively short time (a few hours), regardless of the type of saccharide in the branched portion. Furthermore, since the reaction was conducted under solvent-free conditions using activated carbon, the amount of solvent used in the production of branched CD could be reduced. The branched beta-CDs prepared using the activated carbon catalyst showed high solubility, high solubilization capacity, and low hemolytic activity, similar to the 2-hydroxypropyl-beta-CD used for pharmaceuticals. These results indicate that activated carbon is an industrially and environmentally useful catalyst for branched CD syntheses.
引用
收藏
页码:91 / 99
页数:9
相关论文
共 31 条
[1]   SYNTHESIS OF BRANCHED CYCLOMALTOOLIGOSACCHARIDES USING PSEUDOMONAS ISOAMYLASE [J].
ABE, JI ;
MIZOWAKI, N ;
HIZUKURI, S ;
KOIZUMI, K ;
UTAMURA, T .
CARBOHYDRATE RESEARCH, 1986, 154 :81-92
[2]   NMR-SPECTROSCOPY IN THE STRUCTURAL ELUCIDATION OF OLIGOSACCHARIDES AND GLYCOSIDES [J].
AGRAWAL, PK .
PHYTOCHEMISTRY, 1992, 31 (10) :3307-3330
[3]   A SIMPLE AND RAPID METHOD FOR THE PERMETHYLATION OF CARBOHYDRATES [J].
CIUCANU, I ;
KEREK, F .
CARBOHYDRATE RESEARCH, 1984, 131 (02) :209-217
[4]   Carbohydrate structural determination by NMR spectroscopy: Modern methods and limitations [J].
Duus, JO ;
Gotfredsen, CH ;
Bock, K .
CHEMICAL REVIEWS, 2000, 100 (12) :4589-+
[5]  
Hamaguchi N., 2015, Journal of Applied Glycoscience, V62, P7
[6]   Enzymatic synthesis of N-acetylglucosaminyl-cyclodextrin by the reverse reaction of N-acetylhexosaminidase from jack bean [J].
Hamayasu, K ;
Fujita, K ;
Hara, K ;
Hashimoto, H ;
Tanimoto, T ;
Koizumi, K ;
Nakano, H ;
Kitahata, S .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1999, 63 (10) :1677-1683
[7]   Enzymatic synthesis of mannosyl-cyclodextrin by alpha-mannosidase from jack bean [J].
Hamayasu, K ;
Hara, K ;
Fujita, K ;
Kondo, Y ;
Hashimoto, H ;
Tanimoto, T ;
Koizumi, K ;
Nakano, H ;
Kitahata, S .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1997, 61 (05) :825-829
[8]  
Higuchi T., 1965, Advances in Analytical Chemistry and Instrumentation, V4, P117, DOI DOI 10.1016/S0076-6879(82)87029-8
[9]   Preparation and characterization of novel branched β-cyclodextrins having β-D-galactose residues on the non-reducing terminal of the side chains and their specific interactions with peanut (Arachis hypogaea) agglutinin [J].
Ikuta, A ;
Mizuta, N ;
Kitahata, S ;
Murata, T ;
Usui, T ;
Koizumi, K ;
Tanimoto, T .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2004, 52 (01) :51-56
[10]   Pharmaceutical applications of cyclodextrins .3. Toxicological issues and safety evaluation [J].
Irie, T ;
Uekama, K .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1997, 86 (02) :147-162