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- W2017031106 abstract "Abstract Per‐6‐amino‐2,3‐dimethyl‐ß‐cyclodextrin was prepared very efficiently as its hydrochloride salt from native ß‐cyclodextrin in four steps and 89% overall yield. O ‐Acetyl‐protected ß‐D‐thioglucose and ß‐D‐thiolactose derivatives, containing short spacer arms terminated with carboxylic acid functions, were prepared by the BF 3 ·OEt 2 ‐catalyzed thioglycosylation of ß‐D‐glucose pentaacetate and ß‐lactose octaacetate with 3‐mercaptopropionic acid, respectively. Utilizing amide bond formation as the key step, these thio‐ß‐D‐glucosyl and lactosyl derivatives were coupled to per‐6‐amino‐2,3‐dimethyl‐ß‐cyclodextrin to afford, after deprotection, perfunctionalized ß‐cyclodextrin‐based clusters containing seven thio‐ß‐D‐glucosyl and seven ß‐lactosyl appendages, respectively. Molecular modeling of both these ß‐cyclodextrin‐based clusters revealed the glucose and lactose clusters to be approximately 23 Å and 27 Å in diameter, respectively, and approximately 19 Å in height in both cases. The association constants for the complexation of the anti‐inflammatory drug naproxen by ß‐cyclodextrin, per‐2,3‐dimethyl‐ß‐cyclodextrin, and the lactose cluster of ß‐cyclodextrin in 0.01 M phosphate buffered saline solution (pH 7.4) were found by UV‐vis spectrophotometric titration to be 374 ± 75 M −1 , 351 ± 70 M −1 , and 165 ± 33 M −1 , respectively." @default.
- W2017031106 created "2016-06-24" @default.
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- W2017031106 date "2000-12-01" @default.
- W2017031106 modified "2023-10-17" @default.
- W2017031106 title "Cyclodextrin‐based carbohydrate clusters by amide bond formation" @default.
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- W2017031106 doi "https://doi.org/10.1560/26tf-06hg-eqjj-w85j" @default.
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