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Epimer

Epimers are diastereomers that differ in configuration at only one stereogenic center. Examples of epimers include the sugars α-glucose and β-glucose, which differ in the orientation of their hydroxyl groups. The stereoisomers β-D-glucopyranose and β-D-mannopyranose are also epimers as they differ only in the stereochemistry of their C-2 hydroxyl group. Closely related drug compounds doxorubicin and epirubicin are epimers of each other. Epimerisation is a chemical process where an epimer is transformed into its chiral counterpart, which can occur spontaneously or be catalyzed by enzymes.

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101 views2 pages

Epimer

Epimers are diastereomers that differ in configuration at only one stereogenic center. Examples of epimers include the sugars α-glucose and β-glucose, which differ in the orientation of their hydroxyl groups. The stereoisomers β-D-glucopyranose and β-D-mannopyranose are also epimers as they differ only in the stereochemistry of their C-2 hydroxyl group. Closely related drug compounds doxorubicin and epirubicin are epimers of each other. Epimerisation is a chemical process where an epimer is transformed into its chiral counterpart, which can occur spontaneously or be catalyzed by enzymes.

Uploaded by

Ronit Singh
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© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
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Epimer

From Wikipedia, the free encyclopedia

In chemistry, epimers are diastereomers that differ in configuration of only one stereogenic center. Diastereomers are a class of stereoisomers that are non-superimposable, non-mirror images of one another.[1] [2] In chemical nomenclature, one of the epimeric pairs is given the prefix epi- for example in quinine and epiquinine. When the pairs are enantiomers, the prefix becomes ent-.

[edit]Examples
The sugars -glucose and -glucose are epimers. In -glucose, the -OH group on the first (anomeric) carbon is in the direction opposite the methylene group on carbon C-6 (in the axial position). In -glucose, the -OH group is oriented in the same direction as the methylene group (in the equatorial position). [3] These two molecules are both epimers and anomers (as indicated by the -glucose and designation).

-D-glucopyranose

-D-glucopyranose

The stereoisomers -D-glucopyranose and -D-mannopyranose are epimers because they differ only in the stereochemistry at the C-2 position. The hydroxyl group in -D-glucopyranose is equatorial (in the "plane" of the ring) while in -D-mannopyranose the C-2 hydroxyl group is axial (up from the "plane" of the ring). These two molecules are epimers but, because not mirror images of each other, are also not enantiomers (enantiomers have the same name but differ in D and L classification). They are also not sugar anomers, since the wrong carbon is involved in the stereochemistry.

-D-glucopyranose

-D-mannopyranose

Doxorubicin and epirubicin are two closely related drugs and epimers.

Doxorubicinepirubicin comparison

Other closely related compounds are epi-inositol and inositol and lipoxin and epilipoxin.

Epi-inositol [edit]Epimerisation

Inositol

Lipoxin

Epilipoxin

Epimerisation is a chemical process where an epimer is transformed into its chiral counterpart. It can happen in condensed tannins depolymerisation reactions. Epimerisation can be spontaneous (generally a slow process), or catalyzed by enzymes, e.g. the epimerization between the sugars N-acetylglucosamine and N-acetylmannosamine, which is catalyzed by Renin-Binding Protein.

[edit]References

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