Threose
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Threose is a four-carbon monosaccharide with molecular formula C4H8O4. It has a terminal aldehyde group, rather than a ketone, in its linear chain and so is considered part of the aldose family of monosaccharides. The threose name can be used to refer to both the <templatestyles src="smallcaps/styles.css"/>d- and <templatestyles src="smallcaps/styles.css"/>l-stereoisomers and more generally to the racemic mixture (<templatestyles src="smallcaps/styles.css"/>d/L-, equal parts D- and L-) as well as to the more generic threose structure (absolute stereochemistry unspecified).
The prefix "threo-" which derives from threose (and "erythro-" from a corresponding diastereomer erythrose) offer a useful way to describe general organic structures with adjacent chiral centers, where "the prefixes... designate the relative configuration of the centers".[3] As is depicted in a Fischer projection of <templatestyles src="smallcaps/styles.css"/>d-threose, the adjacent substituents will have a syn orientation in the isomer referred to as "threo", and are anti in the isomer referred to as "erythro".[3][4]
Although often inconsequential, threose in aqueous solution mainly exists as the hydrate owing to the following equilibrium:[5]
See also
References
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- ↑ Merck Index, 11th Edition, 9317
- ↑ Script error: No such module "citation/CS1".
- ↑ a b Formulas Using Other Configurational Notations, W. Rausch, accessed 1 March 2011
- ↑ Prof. Rausch helpfully notes that the prefixes "may be applied to racemic compounds, as well as pure enantiomers and meso compounds", and that when depicted in the common "zig-zag" representation, adjacent "substituents may lie on the same side of the carbon chain... [syn] or on opposite sides... [anti]", which is opposite of their depiction in a Fischer projection.
- ↑ Script error: No such module "Citation/CS1".
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