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词条 Threose
释义

  1. See also

  2. References

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470609476
| Reference = [1]
| ImageFile1 = D-threose.svg
| ImageSize1 = 150px
| ImageCaption1 = D-Threose
| ImageFile2 = L-threose.svg
| ImageSize2 = 150px
| ImageCaption2 = L-Threose
| IUPACName = (2S,3R)-2,3,4-Trihydroxybutanal (D)
(2R,3S)-2,3,4-Trihydroxybutanal (L)
| OtherNames = Threotetrose
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 388736
| InChI = 1/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4-/m1/s1
| InChIKey = YTBSYETUWUMLBZ-QWWZWVQMBY
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YTBSYETUWUMLBZ-QWWZWVQMSA-N
| CASNo = 95-43-2
| CASNo_Ref = {{cascite|changed|??}}
| CASNo_Comment = (D)
| CASNo1 = 95-44-3
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1_Comment = (L)
| PubChem = 439665
| PubChem_Comment = (D)
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28587
| SMILES = O=C[C@@H](O)[C@H](O)CO
| SMILES_Comment = (D)
| SMILES1 = OC[C@H](O)[C@@H](O)C=O
| SMILES1_Comment = (L)
}}
|Section2={{Chembox Properties
| C=4 | H=8 | O=4
| Appearance = Syrup
| Density =
| MeltingPt =
| BoilingPt =
| Solubility = Very soluble
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}

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 D- and L-stereoisomers, and more generally to the racemic mixture (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".[2] As is depicted in a Fischer projection of 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".[2][3]

{{clear-left}}

See also

  • Threonic acid
  • Threose nucleic acid

References

1. ^Merck Index, 11th Edition, 9317
2. ^Formulas Using Other Configurational Notations, W. Rausch, accessed 1 March 2011
3. ^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.
{{Carbohydrates}}

1 : Aldotetroses

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