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Carbohydrate Nomenclature I.

Monosaccharides
Taming the Mayhem
We may think of carbohydrates as sugar and spice and everything
nice, but, to first year biochemistry students, carbohydrates are a terror. One
reason is the nomenclature for the monosaccharides. A comprehensive
nomenclature is needed to obtain precision in a classification scheme,
distinguishing one sugar from another when only subtle differences exist
between the two. Organic chemistry gives us terms such as D and L isomers,
chiral centers, enantiomers, diastereoisomers, etc. Biochemical terminology
builds on the organic using terms such as anomers, alpha and beta sugars,
glycosides, oligosaccharides, all attempting to signify uniqueness in the
complexity of the structures. Sprinkled in among the vocabulary are specific
names of sugars, e.g., glucose, maltose, amylopectin, that can be as daunting
to learn as the structures. This tutorial is designed to point out features that will
help you remember the structures and names of this all-important class of
biomolecules.
Numbers, Groups and Names
OSE is the suffix denoting a sugar and ULOSE denotes a keto sugar. The
monosaccharides you will encounter in biochemistry have 3, 4, 5, 6, and 7 carbons. Prefixes
such as tri, tetra, penta, hexa, and hepta alert you to the number. Know these prefixes (click
1). You will also see aldo and keto to denote the type of functional group (click 1). The
term aldopentose denotes two structural features, chain length and functional group. Aldo
refers to aldehyde and keto to ketone. The figures show an aldopentose and a ketohexose.
C
C
C
Tri-
C
C
C
C
Tetra-
C
C
C
C
C
Penta-
C
C
C
C
C
C
Hexa-
C
C
C
C
C
C
C
Hepta-
C
C
C
C
C
O
H
Aldopentose
C
C=O
C
C
C
C
Ketohexose
An aldo sugar always has the carbonyl group on C-1, a keto sugar has it on C-2. This is good
to remember. OH groups are not indicated by this terminology. More terms are need,
therefore, to describe a specific sugar. Click to go on.
Balls and Sticks:
All sugars have one carbonyl group and at least two OH groups. All
have at least one CH
2
OH group. What distinguishes one from another is the
right-left orientations of internal OH groups. Stereochemistry is best learned by
using balls and sticks. For example, D-glucose, an aldohexose, is show as (click
1). The ball represents the CHO group, the sticks OH groups. Because a
CH
2
OH group is common to all sugars, it is not necessary to draw this group each
time.
D-glucose
The red line shows the OH group whose left/right orientation determines if its a D- or
L-sugar. L-glucose is the mirror image of D-glucose (click 1). Focus on chiral center
orientations to learn the sugars. Keto sugars can only be represented by sticks, with
a = to show the keto group (click 1). Ball and stick representations are a quick way
to help you see differences between sugars and imprint these in you memory (click 1)
L-glucose D-fructose D-ribose D-mannose L-mannose
Rules for Configurations
What you saw on the previous slide was the importance of OH group
orientation to pinpoint a specific sugars name. Now you will see that internal
configurations have their own prefixes, such as gluco, manno, galacto, fructo,
etc. Configuration prefixes help you compare sugars. Here are examples of D
sugar configurations (click 1).
Note that glucose and galactose differ
by orientation around C-4 (click 1) and
glucose and mannose differ at C-2
(click 1). The other aldohexoses are
allose with all OH groups on the same
side (click 1) to idose (the idiot sugar)
that can decide which side to put its
OH groups (click 1).
gluco galacto manno gulo allo ido altro talo
ribo xylo arabino lyxo erythro threo fructo
In the pentoses, one sees that
ribose has all OH groups on the
same side (click 1). The tetroses
differ by orientation around C-2.
Fructose is set apart because of
the keto group on C-2 (click 1).
But, note that C-3 to C-6 of
fructose have the same
configuration as glucose (click 1).
Click to go on.
D vs L Classification Simplifies Names
Recall, aldohexoses have 4 chiral centers, or 16 (2
4
) stereoisomers possible. Does
that mean 16 individual sugar names? No. When we denote aldohexoses as D or L, only 8 (2
3
)
D-steroisomers are possible. This is because the D, L designation fixes one of the centers.
Therefore, of the 16, 8 D and 8 L will have the same name. Common aldohexoses you will
encounter in your studies are D-glucose, D-mannose, and D-galactose. Know these and D-
fructose (click 1).
Applying the same rule, there are 4, D-aldopentoses and 2, D-aldotetroses. The common D-
aldopentoses are D-ribose and D-xylose (pronounced zy-lose) (click 1). If you use your
imagination you should see an X in the structure of xylose (click 1). Perhaps calling xylose
the idiot sugar of pentoses will help you remember the structure. The aldotetroses are
represented by D-erythrose and D threose (click 1). D-erythrose, like D-ribose has all OH
groups on the right. D-threose has one right and one left (another idiot sugar?). Click to go
on.
D-ribose D-xylose D-erythrose D-threose D-glucose L-glucose D-galactose D-mannose D-fructose
Rings
Only 5-, 6-, and 7-carbon sugars form rings. The ring can either have 6 atoms
(pyranose) or 5 atoms (furanose). The OH group on a hexose will attack C-1 to form a ring
(click 1). When the ring forms, a new asymmetric carbon is introduced into the molecule
(click 1). The OH on the new asymmetric carbon can be drawn so as to appear on the
same side of the ring-forming oxygen (alpha sugar) (click one), or it can be drawn to be on
the side away from the ring-forming oxygen (beta sugar) (click 1).
C
C
C
C-OH
C-OH
CH
2
OH
O
H
HO-
-OH
C
C
C-OH
C
C-OH
CH
2
OH
OH
H
O
alpha D-glucopyranose
HO-
C
C
C-OH
C
C-OH
CH
2
OH
H
O
HO
beta D-glucopyranose
HO-
You should now be able to see how all the nomenclature discussed thus far is needed to
pin down a specific monosaccharide. To help you see this, consider the alternatives to
alpha D-glucose. Its alpha (not beta), D (not L), gluco (not galacto, manno, fructo, etc.)
pyranose (not furanose). The nomenclature is precise for just one sugar. Click one to
go on.
*
Terminology
We end the lesson by considering the terminology that describes the
properties of sugars. Understand that terminology is needed to draw comparisons
between structures. So, the question you must ask is how does this term tell me how
two sugars differ? Remember isomers must have something in common as well as
different.
1. Glucose and galactose are epimers (click 1).
The word epimer is used when comparing sugars with multiple chiral centers. It literally
says only one center is different.
2. L-glucose is the enantiomer of D-glucose (click 1)
This means that one is the mirror image of the other.
3. Alpha D-glucose is the anomer of beta D-glucose (click 1)
Anomers differ in the stereochemistry around the ring-forming carbon. Since alpha and beta
differ in only one chiral center, anomers can also be considered epimers
4. Glucose and galactose are diastereoisomers (click 1)
Diastereoisomers have different physical properties. Generally optical isomers with one chiral
center differ only in the direction they rotate plane-polarized light. Diastereoisomers differ both in
rotation and physical properties. D-galactose and D-glucose, for example have the same
chemical formulas (C
6
H
12
O
6
), the same straight carbon chain and the same number of OH
groups. But, besides rotation, they also differ in melting point, solubility, heat of vaporization, etc.
That is why they are considered dia (lit., opposed to being simple) stereoisomers.
Test and Extend Your Understanding
Q: Dont make the mistake of thinking that left/right orientation of the critical OH group
changes a D into an L sugar. To show this, what sugar would you form if C-5 on D-glucose
was oriented to the left instead of the right?
A: L-idose
Q: Are D-glucose and D-ribose isomers? If so, what term describes the relationship?
A: D-glucose and D-ribose are not isomers of one another because they have different chemical
formulas. To be considered a structural or stereoisomer, the two molecules must have the same
empirical formula but differ only in the positioning of the atoms.
Q: What is the relationship between D-glucose and D-fructose?
A: This is a tough call. Both have the same formula and both have a carbonyl functional group. D-
glucose has an aldehyde as its functional group and D-fructose has a ketone. The two must, therefore,
be considered structural isomers and not stereoisomers.
Q: How many epimers are there of D-glucose? Of -D-glucose?
A: Two, D-mannose and D-galactose. -D-glucose has 3: -D-glucose, -D-mannose, -D-galactose.
Q: How many stereoisomers of a heptulose are possible? How many are D and how many
are L sugars? How many names will be needed for all the isomers? (hint: the name tells you
the structure of this sugar).
A: A heptulose is a 7 carbon keto sugar. Therefore, it has 4 chiral centers, which means the straight
chain form has 16 isomers; 8 are D and 8 are L, just like glucose. There will be 8 names needed.