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Difference between revisions of "Conformational nomenclature"

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(Added 1980 IUPAC Nomenclature ref.)
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* [[Responsible Curator]]:  [[User:SpencerWilliams|Spencer Williams]]
 
* [[Responsible Curator]]:  [[User:SpencerWilliams|Spencer Williams]]
 
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The conformations adopted by a pyranose or furanose ring are denoted by a system in which a capital letter indicates the overall shape, ''C'' = chair, ''B'' = boat, ''H'' = half chair, ''S'' = skew boat, ''E'' = envelope <cite>IUPACNomenclature1981</cite>.  The first four of these conformations has four atoms in a plane; the envelope conformation has five.
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The conformations adopted by a pyranose or furanose ring are denoted by a system in which a capital letter indicates the overall shape, ''C'' = chair, ''B'' = boat, ''H'' = half chair, ''S'' = skew boat, ''E'' = envelope <cite>IUPACNomenclature1981 IUPACNomenclature1980</cite>.  The first four of these conformations has four atoms in a plane; the envelope conformation has five.
  
 
The particular conformation is then denoted by assigning the letter corresponding to the shape (''C'', ''B'', ''H'', ''S'', ''E''); determining the four (or five) atoms that define the plane; assigning a 'top' and 'bottom' face through the use of a left-hand rule counting in the order of increasing ring carbon; and then indicating the identities and relative positions (top face = superscript and prefix; bottom face = subscript and suffix) of the remaining two atoms on that capital letter. In the case of the envelope conformation, only a single atom is located outside of the plane. For a more detailed discussion see the excellent book by J. Fraser Stoddard <cite>Stoddart1971</cite>.
 
The particular conformation is then denoted by assigning the letter corresponding to the shape (''C'', ''B'', ''H'', ''S'', ''E''); determining the four (or five) atoms that define the plane; assigning a 'top' and 'bottom' face through the use of a left-hand rule counting in the order of increasing ring carbon; and then indicating the identities and relative positions (top face = superscript and prefix; bottom face = subscript and suffix) of the remaining two atoms on that capital letter. In the case of the envelope conformation, only a single atom is located outside of the plane. For a more detailed discussion see the excellent book by J. Fraser Stoddard <cite>Stoddart1971</cite>.
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<biblio>
 
<biblio>
 
#IUPACNomenclature1981 Conformational nomenclature for five- and six-membered ring forms of monosaccharides and their derivatives, Pure and Appl. Chem., 1981, ''53'', 1901—1905.  [http://dx.doi.org/10.1351/pac198153101901 DOI: 10.1351/pac198153101901]
 
#IUPACNomenclature1981 Conformational nomenclature for five- and six-membered ring forms of monosaccharides and their derivatives, Pure and Appl. Chem., 1981, ''53'', 1901—1905.  [http://dx.doi.org/10.1351/pac198153101901 DOI: 10.1351/pac198153101901]
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#IUPACNomenclature1980 pmid=7460897
 
#Stoddart1971 Stereochemistry of Carbohydrates, J. Fraser Stoddart, John Wiley & Sons Inc, 1971, 264 pages.
 
#Stoddart1971 Stereochemistry of Carbohydrates, J. Fraser Stoddart, John Wiley & Sons Inc, 1971, 264 pages.
 
</biblio>
 
</biblio>
 
[[Category:Definitions and explanations]]
 
[[Category:Definitions and explanations]]

Revision as of 07:22, 4 August 2013

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The conformations adopted by a pyranose or furanose ring are denoted by a system in which a capital letter indicates the overall shape, C = chair, B = boat, H = half chair, S = skew boat, E = envelope [1, 2]. The first four of these conformations has four atoms in a plane; the envelope conformation has five.

The particular conformation is then denoted by assigning the letter corresponding to the shape (C, B, H, S, E); determining the four (or five) atoms that define the plane; assigning a 'top' and 'bottom' face through the use of a left-hand rule counting in the order of increasing ring carbon; and then indicating the identities and relative positions (top face = superscript and prefix; bottom face = subscript and suffix) of the remaining two atoms on that capital letter. In the case of the envelope conformation, only a single atom is located outside of the plane. For a more detailed discussion see the excellent book by J. Fraser Stoddard [3].

Conformations.png

References

  1. Conformational nomenclature for five- and six-membered ring forms of monosaccharides and their derivatives, Pure and Appl. Chem., 1981, 53, 1901—1905. DOI: 10.1351/pac198153101901
    [IUPACNomenclature1981]
  2. (1980) IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). Conformational nomenclature for five and six-membered ring forms of monosaccharides and their derivatives: recommendations 1980. Eur J Biochem. 111, 295-8. DOI:10.1111/j.1432-1033.1980.tb04941.x | PubMed ID:7460897 | HubMed [IUPACNomenclature1980]
  3. Stereochemistry of Carbohydrates, J. Fraser Stoddart, John Wiley & Sons Inc, 1971, 264 pages.
    [Stoddart1971]