Chemistry:Cyclodextran
Cyclodextran, also known as cyclic isomaltooligosaccharide (CI), is a cyclic oligosaccharide composed of glucose units linked primarily by α-1,6 glycosidic bonds. It is a non-reducing carbohydrate derived from dextran or related glucans through enzymatic cyclization.
Structure and nomenclature
Cyclodextran is distinct from cyclodextrin, another class of cyclic glucose oligomers, in its linkage pattern. Whereas cyclodextrins are composed of α-1,4-linked glucose units, cyclodextrans consist of α-1,6-linked glucose units. Reported cyclodextrans vary in ring size, and multiple homologues have been identified.[1]
Discovery and production
Cyclodextran was first reported in 1993 during studies of bacterial cultures grown on dextran-containing media. It was identified as a cyclic product distinct from linear isomaltooligosaccharides.[2]
Trace amounts of cyclodextran have also been reported from brown sugar.[3]
Cyclodextran is produced by enzymatic conversion of dextran, typically through the action of cycloisomaltooligosaccharide glucanotransferase (CITase). Some studies have also described pathways in which related enzymes generate cyclodextrans from starch-derived glucans.[4][5]
Properties
As a cyclic carbohydrate, cyclodextran lacks a reducing end and is classified as a non-reducing oligosaccharide. It is water-soluble and relatively stable under a range of chemical conditions.[5] Studies have also examined its ability to interact with other compounds in aqueous systems.[6]
Cyclodextran has also been examined in studies of glucan-related processes in oral bacteria.[7]
References
- ↑ "Isolation of Bacillus and Paenibacillus Bacterial Strains That Produce Large Molecules of Cyclic Isomaltooligosaccharides". Bioscience, Biotechnology, and Biochemistry 72 (12): 3277–80. December 2008. doi:10.1271/bbb.80384. PMID 19060390.
- ↑ "Novel Cyclic Dextrins, Cycloisomaltooligosaccharides, from Bacillus sp. T-3040 Culture". Bioscience, Biotechnology, and Biochemistry 57 (7): 1225–27. January 1993. doi:10.1271/bbb.57.1225. PMID 27281012.
- ↑ "Novel Cycloisomaltooligosaccharides Contained in the Kokuto Produced in Okinawa Prefecture". Journal of Applied Glycoscience 54 (1): 27–30. 2007. doi:10.5458/JAG.54.27.
- ↑ "Paenibacillus sp. 598K 6-α-glucosyltransferase is essential for cycloisomaltooligosaccharide synthesis from α-(1 → 4)-glucan". Applied Microbiology and Biotechnology 101 (10): 4115–4128. 2017. doi:10.1007/s00253-017-8174-z. PMID 28224195.
- ↑ 5.0 5.1 Oguma, Tetsuya; Kawamoto, Hiroshi (2003). "Production of Cyclodextran and Its Application". Trends in Glycoscience and Glycotechnology 15 (82): 91–99. doi:10.4052/tigg.15.91. https://www.jstage.jst.go.jp/article/tigg1989/15/82/15_82_91/_article/-char/en/.
- ↑ Hong, Seong-Jin; Park, Bo-Ram; Lee, Byung-Hoo; Park, Boo-Su; Kim, Young-Min (2023). "New Potential Applications of Cyclodextran in High Water Solubility and in Vitro Digestive System". SSRN. https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4477437.
- ↑ Kobayashi M; Funane K; Oguma T (1995). "Inhibition of Dextran and Mutan Synthesis by Cycloisomaltooligosaccharides". Bioscience, Biotechnology, and Biochemistry 59 (10): 1861–65. doi:10.1271/bbb.59.1861. PMID 8534976.
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