Abstract
This Highlight describes the detailed approach used to determine the absolute stereochemistry of the stereogenic centers in the acyclic side chain of kotalanol, a naturally occurring glucosidase inhibitor isolated from the plant Salacia reticulata. The plant extract itself is used in Ayurvedic medicine for the treatment of Type 2 diabetes. We highlight the syntheses of proposed candidates based on structure-activity relationships, the total synthesis of kotalanol, and crystallographic studies of kotalanol and its de-O-sulfonated derivative complexed with recombinant human maltase glucoamylase (MGA), a critical intestinal glucosidase involved in the breakdown of glucose oligomers into glucose.
Publication types
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Research Support, Non-U.S. Gov't
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Review
MeSH terms
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Biological Products* / chemistry
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Biological Products* / isolation & purification
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Biological Products* / pharmacology
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Diabetes Mellitus, Type 2 / drug therapy
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Diabetes Mellitus, Type 2 / enzymology
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Glucosidases / antagonists & inhibitors*
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Glucosidases / metabolism
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Glycoside Hydrolase Inhibitors*
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Humans
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Intestines / enzymology
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Medicine, Ayurvedic
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Molecular Structure
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Monosaccharides* / chemistry
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Monosaccharides* / isolation & purification
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Monosaccharides* / pharmacology
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Salacia / chemistry*
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Stereoisomerism
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Structure-Activity Relationship
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Sulfates* / chemistry
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Sulfates* / isolation & purification
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Sulfates* / pharmacology
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alpha-Glucosidases / metabolism
Substances
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Biological Products
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Glycoside Hydrolase Inhibitors
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Kotalanol
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Monosaccharides
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Sulfates
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Glucosidases
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alpha-Glucosidases