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Aldose
Ketose
aldotriose
ketotriose
aldotetrose
ketotetrose
aldopentose
ketopentose
aldohexose
ketohexose
In addition to these names each of the simple sugars has a common name.
Glyceraldehyde is an aldotriose. Glucose is an aldohexose. Fructose is a
ketohexose. Galactose is an aldohexose. Ribose is an aldopentose
Stereoisomerism
Isomers are compounds with identical molecular formulas. Isomers can be
categorized into the two different groups of constitutional isomers or
stereoisomers.
Constitutional isomers have the same molecular formula but a different
molecular framework (different bonding constitution). Because constitutional
isomers have different bonding constitutions, they are different molecules.
This means that constitutional isomers have different physical and chemical
properties. Ethanol CH3CH2OH and dimethyl ether CH3OCH3 are constitutional
isomers. Both have the same molecular formula (C2H6O) but differ in how the
atoms are connected.
Stereoisomers are molecules containing the same atoms bonded identically
but the bonded atoms are oriented differently in space. That is to say, they
have identical bonding constitutions but differ in how the atoms are oriented
in the space around the atoms to which they are bonded.
molecule.
Important Monosaccharides
D-Glyceraldehyde an aldotriose is the simplest carbohydrate. It has one
stereogenic center. It is a sweet colorless crystalline solid, C3H6O3, that is an
intermediate compound in carbohydrate metabolism. D-glyceraldehyde is
the arbitrarily chosen standard for the assignment of the D configuration. In
a D sugar, the hydroxy functional group is on the right side of the
asymmetric carbon atom. D-glyceraldehyde (D for dextrorotatory) rotates
light to the right.
Cyclic hemiacetals are formed if both the hydroxyl and the carbonyl group
are in the same molecule by an intramolecular nucleophilic addition. Five and
six-membered cyclic hemiacetals are particularly stable and many
carbohydrates therefore exist in equilibrium between open-chain and cyclic
forms.
Pyranose is the six-membered cyclic hemiacetal formed from aldohexoses.
(The name comes from the six-membered cyclic ether pyran.) Furanose is
the five-membered cyclic hemiacetal formed by the ketohexose fructose.
(The name comes comes from the five-membered cyclic ether furan.)
Pyranose and furanose rings can be represented by Haworth projections.
Haworth projections are planar representations of the furanose and pyranose
forms of carbohydrates. These type projections allow the cis-trans
relationships among hydroxyl groups to be seen. In which the hemiacetal
ring is drawn as if it were flat and is viewed edge-on with the oxygen atom at
the upper right.
The relationship between a Fischer projection and a Haworth projection is
that the group on the right in a Fischer projection is down in the Haworth
projection. The group on the left in a Fischer projection is up in a Haworth
projection. For D-sugars, the terminal -CH2OH group is always up in Haworth
projections, whereas for L-sugars the terminal -CH2OH group is down.
DNA, the molecule that carries the genetic information of the cell, contains 2deoxyribose. The hydroxy group has been replaced by a hydrogen at carbon
number 2, hence the designation of "2-deoxy."
Reducing sugars
Early biochemists devised analytical methods for the detection and
quantification of sugars. Some of these tests (e.g., Benedicts Test or
Fehling's reagent) were based on the aldehyde or ketone groups in the sugar
structures. Sometimes the test gave a color change as a metal ion was
reduced to the metal itself or to an ion of lower oxidation state. In other
words, the reagent oxidized the sugar while the sugar reduced the oxidation
state of the ions.
A reducing sugar is any sugar which reacts in basic Cu2+ solution to yield
Cu2O precipitate (Benedicts Test). That is, they are sugars that contain
aldehyde groups that can be oxidized to carboxylic acids. All
monosaccharides are reducing sugars. All the common disaccharides, except
sucrose, are reducing sugars. Lactose, maltose, cellobiose are reducing
sugars. Sucrose is not a reducing sugar. Polysaccharides are not reducing
sugars. A sugar must exist as the linear form in solution to be a reducing
sugar.
Disaccharides
Oligosaccharides are formed by joining two to ten monosaccharides.
Aldehydes react with alcohols to form hemiacetals. The hemiacetal can react
further to yield an acetal.