Diastereomer
Non-mirror image stereoisomers with distinct physical and chemical properties.
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Diastereomers are stereoisomers that are not mirror images of each other and are not identical.[1] When stereoisomers are not mirror images and have different configurations at some but not all equivalent stereocenters, they are classified as diastereomers.[2] Enantiomers are mirror-image stereoisomers that differ at every stereocenter, which is not the case for diastereomers.[3]
Quick Facts
- Field
- Stereochemistry
- Related concepts
- Epimers
- enantiomers
- syn/anti
- erythro/threo
- E-Z notation
Facts from the source article.
Key facts and history
The prefixes threo and erythro are older terms still used to distinguish diastereomers.[4] Epimers are a subset of diastereomers that vary at a single stereocenter.[2] Physical properties and chemical reactivity are not the same for diastereomers.[5] The four-carbon aldoses erythrose and threose, which are diastereomers, are the source of the prefixes erythro and threo.[6]
In an organic reaction, diastereoselectivity refers to the favored production of one diastereomer over another.[7]
References
- Wikipedia, "Diastereomer" (CC BY-SA 4.0), which cites: IUPAC "Gold Book" diastereoisomerism (we also read that source) en.wikipedia.org
- Wikipedia, "Diastereomer" (CC BY-SA 4.0), which cites: Garrett, "Biochemistry 3rd ed.", Thomson, 2005, p. 205 (we also read that source) en.wikipedia.org
- Wikipedia, "Diastereomer" (CC BY-SA 4.0), which cites: IUPAC "Gold Book" enantiomer (original not read by us) en.wikipedia.org
- Wikipedia, "Diastereomer" (CC BY-SA 4.0), which cites: Modern physical organic chemistry Eric V. Anslyn, Dennis A. Dougherty 2006 (original not read by us) en.wikipedia.org
- Wikipedia, "Diastereomer" (CC BY-SA 4.0), which cites: McCance, "The comparative rates of absorption of sugars from the human intestine", Biochemical Journal, 1930, p. 795–804; Chao, "Differentiation and Quantification of Diastereomeric Pairs of Glycosphingolipids using Gas-phase Ion Chemistry", Analytical Chemistry, 2020-10-06, p. 13387–13395 (we also read that source) en.wikipedia.org
- Wikipedia, "Diastereomer" (CC BY-SA 4.0) en.wikipedia.org
- Wikipedia, "Diastereomer" (CC BY-SA 4.0), which cites: Lavinda, "Origin of High Diastereoselectivity in Reactions of Seven-Membered-Ring Enolates", Angewandte Chemie International Edition in English, 2022-03-28 (we also read that source) en.wikipedia.org
Each numbered sentence above was checked against the source it cites before publication. Sentences citing Wikipedia adapt text from the English Wikipedia article Diastereomer (contributors), used under CC BY-SA 4.0; this entry is available under the same licence. Other sources were used for facts only; no text or images are copied from them.
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Sources
Compiled from Wikipedia and the sources listed below. Text from Wikipedia is available under CC BY-SA 4.0; this entry is adapted from it.
- Wikipedia: Diastereomer (CC BY-SA 4.0).
- Word definitions: the , each quoted from its Wikipedia article.
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