10/11/2023 0 Comments Chiral carbon in glucose![]() Stereoisomers (aka optical isomers): Any of two or more compounds with identical molecular formulas and arrangements of atoms that only differ in the spatial arrangement of their atoms they have non-superimposable mirror images.Įnantiomers: the same sugars in different optical families (D-glucose and L-glucose).įischer projection: A two-dimensional representation of a molecule that maintains information about its absolute configuration.ĭiastereomers: Two sugars that are in the same family (that are stereoisomers), but are not identical and are not mirror images of each other.Įpimers: A type of stereoisomer that differs in configuration at a single stereogenic center (the anomeric carbon). Epimers are a special subtype of diastereomers that differ in configuration at exactly one chiral center.Ĭhiral carbon (asymmetric carbon):A carbon that is attached to four different types of atoms or groups of atoms.Ībsolute configuration: The three-dimensional arrangement of the groups attached to the chiral carbon in a carbohydrate.Diastereomers are two sugars that are in the same family, but are not identical and are not mirror images of each other.Enantiomers are the same sugars in different optical families (such as D-glucose and L-glucose).In the Fischer projection, all D-sugars have the OH group of their highest-numbered chiral center on the right, and all L-sugars have that OH on the left.The chiral carbon furthest from the carbonyl group determines the absolute configuration L or D of the sugar.D-ribose and D-arabinose are epimers (at carbon number 2), as shown below. Epimers are a special subtype of diastereomers that differ in configuration at exactly one chiral center. Diastereomers are two sugars that are in the same family, but are not identical and are not mirror images of each other. Keep in mind that enantiomers are the same sugars in different optical families (such as D-glucose and L-glucose). If it’s pointing right, then it’s the D form. If the OH group on the chiral carbon furthest from the carbonyl is pointing left, then it’s described as the L form. The Fischer projection is a simple two-dimensional drawing of a molecule’s stereoisomers. The number of possible stereoisomers of a compound can be calculated by:įor example, for a molecule with 1 chiral carbon, the number of stereoisomers is 2 1 = 2 and for a molecule with 2 chiral carbons, the number of stereoisomers is 2 2 = 4. Take a look at the figure below to see an example of the two enantiomers of the carbohydrate glyceraldehyde.Īs seen above, there is only one chiral carbon present, and so these are the only two stereoisomers that exist for glyceraldehyde. These two configurations are the enantiomers. The chiral carbon furthest from the carbonyl group determines the absolute configuration L or D of the sugar. All carbohydrates contain at least one asymmetrical (chiral) carbon. In this regard, D-glyceraldehyde (which happens. Molecules that are mirror images of each other are enantiomers these are molecules that contain chiral carbons and no internal planes of symmetry. But now the letters D and L describe the stereochemistry at a specific chiral carbon atom in a carbohydrate. Stereoisomers are compounds that have the same chemical formula but their molecules differ from one another in terms of the spatial arrangement of their component atoms. 2002, 287, 360.The three-dimensional arrangement of the groups attached to the chiral carbon determines the absolute configuration (D- and L-) of the carbohydrate. This study provides an electrochemical method to facilely regulate CDs chirality, and explore new applications of chiral CDs as antihyperglycemic therapy for controlling blood glucose levels.Ĭarbon dots chirality regulation maltose enzyme activity α-glucosidase inhibitors. The superior performance may be attributed to the preferable combination of DCDs with maltase. At last, the resultant (+)-DCDs (700 µg mL -1 ) are employed to modify maltase in an effort to regulate the hydrolytic rate of maltose, showing an excellent inhibition ratio to maltase of 54.7%, significantly higher than that of (-)-LCDs (15.5%) in the same reaction conditions. Interestingly, their chirality can be regulated by simply adjusting reaction time. Here, chiral CDs with optical rotation opposite to that of the precursor are facilely prepared through electrochemical polymerization. Moreover, in previous reports, chiral CDs with targeted optical activity have to be synthesized from precursors of corresponding optical rotation, severely limiting chiral CDs design. However, the impact of CDs chirality on maltase and blood glucose level has not yet been fully emphasized and studied. Their therapeutic effect strongly depends on the CDs structure (e.g., size or functional groups). Carbon dots (CDs) have attracted increasing attention in disease therapy owing to their low toxicity and good biocompatibility.
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