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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. [ 1 ]
A furanose is a collective term for carbohydrates that have a chemical structure that includes a five-membered ring system consisting of four carbon atoms and one oxygen atom. The name derives from its similarity to the oxygen heterocycle furan , but the furanose ring does not have double bonds .
Ribose can either be a five membered ring or a six membered ring . The furanose form is more useful for cells, as it can be used in other reactions. For most cells, ribose is transported into the cell in the pyranose form. With this said, D-Ribose Pyranase needs to be present to convert the pyranose form into the furanose form.
In these abbreviated forms, the names of the monosaccharide units are shortened to their corresponding three-letter abbreviations, followed by p for pyranose or f for furanose ring structures, with the abbreviated aglyconic alcohol placed at the end of the name. [2]
D-ribose in itself is a hemiacetal and in equilibrium with the pyranose 3. In aqueous solution ribose is 75% pyranose and 25% furanose and a different acetal 4 is formed. Selective acetalization of carbohydrate and formation of acetals possessing atypical properties is achieved by using arylsulfonyl acetals.
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The reaction turns the =O group into a hydroxyl, and the hydroxyl into an ether bridge (−O−) between the two carbon atoms, thus creating a ring with one oxygen atom and four or five carbons. If the cycle has five carbon atoms (six atoms in total), the closed form is called a pyranose, after the cyclic ether tetrahydropyran, that has the ...
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