- Practical Synthesis of the Fluorogenic Enzyme Substrate 4-Methylumbelliferyl α- L -Idopyranosiduronic Acid
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A practical and concise synthesis of 4-methylumbelliferyl α- l -idopyranosiduronic acid, a fluorogenic enzyme substrate diagnostic for α- l -iduronidase, was accomplished. It features successive radical bromination and radical reduction of easily accessible methyl 4-methyl umbelliferyl-2,3,4-tri- O -acetyl-β- d -glucouronate in four steps with 28percent overall yield.
- Bai, Jiang,Ding, Haixin,He, Yanling,Ning, Qianqian,Ouyang, Wenliang,Tian, Jiameng,Xiao, Qiang
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supporting information
p. 1083 - 1086
(2020/07/03)
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- Synthetic method of fluorescent glycosidase substrate for determination of alpha-L-iduronidase
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The invention relates to a synthesis method of a fluorescent glycosidase substrate for determination of alpha-L-iduronidase. According to the method, coumarin-beta-D-glucuronide is used as a raw material; the preparation method comprises the following steps: adding N-bromosuccinimide and a chlorinated organic solvent under an illumination condition by using a Wohl-Ziegler free radical reaction, and carrying out reflux stirring; then, spin-drying the organic solvent under reduced pressure; dissolving and extracting by using an organic solvent, collecting an organic phase, spin-drying the solvent, carrying out silica gel column chromatography separation to obtain a brominated compound, carrying out free radical reduction in the organic solvent, spin-drying the solvent, carrying out silica gel column chromatography separation to obtain coumarin-alpha-L-iduronide, and finally removing a protecting group to obtain coumarin-alpha-L-iduronide. The coumarin-alpha-L-iduronide is synthesized bya method of free radical substitution and reduction of coumarin-beta-D-glucuronide for the first time, and the reaction has the characteristics of simplicity and convenience in operation, simple and easily available raw materials, easiness in product separation, high reaction yield and the like.
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Paragraph 0016
(2019/12/29)
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- AN ESTERIFICATION/SAPONIFICATION-BASED METHOD FOR LIPOSOMAL LOADING
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Described herein is a method for loading a hydrophilic compound into liposomes after addition of an alkylester group to form an esterified compound. After loading, the alkylester is hydrolyzed to reform the hydrophilic compound inside the liposomes. Also described is a method for loading drugs under a glucuronide methylester form into liposomes. The glucuronide methylester form of the drug is saponified to a glucuronide form of the drug inside the liposomes for better drug retention. The glucuronide residue conjugated to drugs can be removed inside cells to regenerate the parental drug upon cell uptake, liposomal degradation and enzyme hydrolysis. In case of cancer, this method can be used to safely deliver drugs to tumors.
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Paragraph 0019; 0025; 0076
(2017/08/01)
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- Profiling of glycosidase activities using coumarin-conjugated glycoside cocktails
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Glycosidases are a large subgroup of carbohydrate-processing enzymes that hydrolytically cleave the glycosidic bond. Glycans formed by the action of glycosidases are involved in various biological processes. Genetic abnormalities in glycosidases are associated with inherited diseases. Thus, characterization of the catalytic activities of glycosidases is of great importance. Herein, we describe a simple and rapid approach for determining glycosidase activity profiles using coumarin-conjugated glycoside cocktails.
- Park, Sungjin,Shin, Injae
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p. 619 - 622
(2007/10/03)
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