The normal form of most sugars is in a cyclic hemiacetal form. The preferred form varies from sugar to sugar: some prefer to be a 6-member ring "pyranose", like glucose: acetal.xyz Backgrounds: Black White Stop animation Restart animation Others, like ribose and fructose, prefer the 5-member ring "furanose" form. An important aspect of hemiacetal formation is the production of a new stereocenter at the carbonyl carbon. This is called the anomeric position. In general, both possible isomers are formed. However, the two diastereomers can often be separated. The β-form of D-glucose crystallizes, but after redissolving the pure β form in water it reconverts to an equilibrium mixture of the two anomeric forms; this process is called mutarotation because it can be detected by a change in the optical rotation. Further evidence of the interconversion of open and closed forms is seen in the capacity of aldoses to react with reagents that only attack aldehudes. See Section 24-4 and the discussion of reducing vs. nonreducing sugars; Section 24-6 on the reduction to alditols is another example. |