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Related Concept Videos

Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Stereoisomers02:32

Stereoisomers

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On the basis of mirror symmetry, stereoisomers of an organic molecule can be further classified into diastereomers and enantiomers. Diastereomers are stereoisomers that are not mirror images of each other. Substituted alkenes, such as the cis and trans isomers of 2-butene, are diastereomers, as these molecules exhibit different spatial orientations of their constituent atoms, are not mirror images of each other, and do not interconvert. Here, the interconversion is suppressed due to...
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Stereoisomerism02:52

Stereoisomerism

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Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
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Isomerism02:43

Isomerism

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Isomers are molecules with the same molecular formula but different structural arrangements. Isomers can be further classified into constitutional isomers and stereoisomers. Constitutional isomers differ in the connectivity of their constituent atoms. For example, 2-butanol and diethyl ether are constitutional isomers, as they have the same chemical formula, C4H10O, but differ in the connectivity of the carbon and oxygen atoms. Constitutional isomers have different physical and chemical...
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Isomerism in Alkenes02:01

Isomerism in Alkenes

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Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...
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Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

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Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
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Related Experiment Video

Updated: Jul 2, 2025

Author Spotlight: Investigating Physiological Functions of Vitamin A Transporters Using HPLC-Based Vitamin A Profiling
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Vitamin E: Not only a single stereoisomer.

M Eggersdorfer1, K Schmidt2, S Péter3

  • 1Department of Internal Medicine, University Medical Center Groningen, Groningen, the Netherlands.

Free Radical Biology & Medicine
|February 24, 2024
PubMed
Summary

Vitamin E

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Area of Science:

  • Biochemistry
  • Human Physiology
  • Nutritional Science

Background:

  • The definition of vitamin E is debated, with some arguing only RRR-α-tocopherol possesses physiological activity.
  • Ataxia with Vitamin E Deficiency (AVED) is a condition linked to vitamin E deficiency, historically treated with RRR-α-tocopherol.

Purpose of the Study:

  • To investigate the physiological definition of vitamin E.
  • To evaluate the efficacy and safety of different vitamin E forms beyond RRR-α-tocopherol.

Main Methods:

  • Review of existing literature on vitamin E biological activities and mechanisms.
  • Analysis of the binding affinity of α-tocopherol transfer protein (α-TTP) to various stereoisomers.
  • Examination of clinical data regarding the treatment of AVED with different vitamin E forms.

Main Results:

  • Physiological vitamin E activity is confirmed to be limited to specific α-tocopherol forms.
  • All 2R-stereoisomers of α-tocopherol, not just RRR-α-tocopherol, bind effectively to α-TTP.
  • 2R-forms are retained in human plasma and tissues, unlike rapidly excreted 2S-stereoisomers.
  • AVED has been successfully treated with vitamin E forms other than RRR-α-tocopherol.
  • No safety concerns are associated with the broader definition of vitamin E.

Conclusions:

  • The physiological definition of vitamin E should include all 2R-stereoisomers of α-tocopherol, not exclusively RRR-α-tocopherol.
  • The broader definition of vitamin E has gained scientific and regulatory acceptance.
  • Current evidence supports the safety and efficacy of this inclusive definition for treating vitamin E deficiency.