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Concept
Pyranose
Summary
Pyranose is a collective term for saccharides that have a chemical structure that includes a six-membered ring consisting of five carbon atoms and one oxygen atom. There may be other carbons external to the ring. The name derives from its similarity to the oxygen heterocycle pyran, but the pyranose ring does not have double bonds. A pyranose in which the anomeric OH at C(l) has been converted into an OR group is called a pyranoside.
The pyranose ring is formed by the reaction of the hydroxyl group on carbon 5 (C-5) of a sugar with the aldehyde at carbon 1. This forms an intramolecular hemiacetal. If reaction is between the C-4 hydroxyl and the aldehyde, a furanose is formed instead. The pyranose form is thermodynamically more stable than the furanose form, which can be seen by the distribution of these two cyclic forms in solution.
Hermann Emil Fischer won the Nobel Prize in Chemistry (1902) for his work in determining the structure of the D-aldohexoses. However, the linear, free-aldehyde structures that Fischer proposed represent a very minor percentage of the forms that hexose sugars adopt in solution. It was Edmund Hirst and Clifford Purves, in the research group of Walter Haworth, who conclusively determined that the hexose sugars preferentially form a pyranose, or six-membered, ring. Haworth drew the ring as a flat hexagon with groups above and below the plane of the ring – the Haworth projection.
A further refinement to the conformation of pyranose rings came when Sponsler and Dore (1926) realized that Sachse's mathematical treatment of six-membered rings could be applied to their X-ray structure of cellulose. It was determined that the pyranose ring is puckered, to allow all of the carbon atoms of the ring to have close to the ideal tetrahedral geometry.
This puckering leads to a total of 38 distinct basic pyranose conformations: 2 chairs, 6 boats, 6 skew-boats, 12 half-chairs, and 12 envelopes.
These conformers can interconvert with one another; however, each form may have very different relative energy, so a significant barrier to interconversion may be present.
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