If the carbon chain is long enough,If the carbon chain is long enough, the alcoholthe alcohol at one endat one end
of a monosaccharide can attack theof a monosaccharide can attack the carbonyl groupcarbonyl group at theat the
other end to form a cyclic compound.other end to form a cyclic compound.
When a sixWhen a six--memberedmemberedring is formed, the product of thisring is formed, the product of this
reaction is calledreaction is called
shown in the figure below.shown in the figure below.
When a five-membered ring isformed, it is called a
D-glucose can cyclize in twoways forming either furanose orpyranose structures
The reactions that lead to the formation of aThe reactions that lead to the formation of a pyranosepyranoseor aor a
furanosefuranoseare reversibleare reversible
For exampleFor example
--DD--glucopyranose orglucopyranose or
these anomers are interconverted to give an equilibriumthese anomers are interconverted to give an equilibriummixture that is 63.6%of themixture that is 63.6%of the
--anomer and 36.4%of theanomer and 36.4%of the
The 2:1 preference for theThe 2:1 preference for the
--anomer can be understood byanomer can be understood bycomparing the structures of these molecules.comparing the structures of these molecules.
In theIn the
--anomer, all of the bulkyanomer, all of the bulky --OH orOH or --CHCH
OH substituents lieOH substituents liemore or less within the plane of the sixmore or less within the plane of the six--membered ring.membered ring.
In theIn the
--anomer, one of theanomer, one of the --OH groups is perpendicular to theOH groups is perpendicular to the
plane of the sixplane of the six--membered ring, in a region where it feels strongmembered ring, in a region where it feels strong
repulsive forces from the hydrogen atoms that lie in similarrepulsive forces from the hydrogen atoms that lie in similarpositions around the ring.positions around the ring.
As a result, theAs a result, the
--anomer is slightly more stable than theanomer is slightly more stable than the
There are two possible structures for the pyranose andThere are two possible structures for the pyranose andfuranose forms of a monosaccharide, which are called thefuranose forms of a monosaccharide, which are called the