World Bre

ewing Acad
demy - We
eb-Based Concise
C Co
ourse in Brrewing
S
Supplemen
ntary Inforrmation

Date
e Created: May 18, 20
007

Mod dule # #3
Title
e of Module B
Basic Brewin
ng Biochemisstry
Topiic (Key Worrds) Molecullar diagramss, Hexagon Diagrams,
D Baackbone arraangement

Thiss shows an example

e of how
h to desccribe molecu
ules, starting with a sim
mple ‘backb
bone’ arranggement and
d
then
n moving intto a “hexagoon diagrams”

You
u can see the source of this infoormation at http
p://campus.norrthpark.edu/bioology/cell/carboh
hydrates.html

The monomer
m for caarbohydrates iss the monosacccharide. There are many diffeerent monosacccharides, but thhey are all simiilar in form.
Monoosaccharides arre commonly known
k as the siimple sugars.

All monosaccharide
m mula (CH2O)n . This states thhat any numberr [n] of carbon atoms may be present on thee carbon
es have the form
'backbbone' of the moolecule. There is an equal nuumber of oxygeen atoms as carrbons, and twicce as many hyddrogens as carbbons. The
simpllest substance that
t matches th he monosacchaaride formula iss CH2O, a subsstance named formaldehyde.
f In the most coommon usage,
ydrates are buiilt on 3-carbon backbones. Thhe most common monosacchharides in cellullar systems
howeever, the smalleest true carbohy
have 3-carbon, 5-caarbon, or 6-carbbon chains.

Glucoose is a hexosee [6-carbon] sugar. Its molecuular formula is (CH2O)6 or C6H12O6. the struuctural formulaa for glucose iss

T critical features that disstinguish onee hexose monoosaccharide from

The f another area the positioons of the carrbonyl and
hydroxyl groups associated with
w the carboon backbone. Each isomer has its own name, n and thoough identicall in size and
weight, each has a diifferent 3-dim
mensional shappe and each reacts
r slightlyy differently inn living systeems.

Page 1 of 4
One isomer of gluucose is fructo ose. The criticcal differencee between glucose and frucctose is the poosition of the carbonyl
groupp. In glucose,, the carbonyll group is on the
t #1 carbonn [the end carbbon of the chain]. Glucosee is therefore classified
c as
an aldehyde or as an aldose sug gar. In fructosse, the carbonnyl group is on the #2 carbon [a central carbon] and fructose
f is
classified as a ketoone or as a keetose sugar.

Glucose and otherr monosacchaarides often foorm ring strucctures when inn solution... It
I is common to show glucoose in either
its linnear or its ring form. The ring
r forms whhen a hydrogeen atom is transferred from
m the hydroxyyl group on thhe #5 carbon
to thee oxygen of thhe carbonyl group
g on the #1
# carbon. Thhis allows the #1 carbon to form a bond with the oxyygen attached
to thee #5 carbon, completing
c th
he ring.

Someetimes the draawings showiing monosacccharides are simplified to show

s only thee most importtant parts of thhe molecules.
The same
s sequencce of events diagrammed
d a
above could be
b shown as:

Here the hydrogenns that complete each moleecule are simpply 'understoood' to be present, and are not
n included in the
diagrrams.

The diagrams
d can be still furtheer simplified by showing only
o the carboons and the caarbonyl groupp [or the oxyggen that is
built into the ring]].

Page 2 of 4
Someetimes even the carbons arre not labelledd, but are assuumed to be prresent at everyy 'bend or endd' of the ring. Simple
hexaggon diagramss such as thosse below can serve
s as highlly simplified models of thee glucose mollecule.

Two [or more] moonosaccharidees may be joinned by dehyddration syntheesis to producce larger disacccharides andd
polyssaccharides. A typical disaaccharide [or double sugar]] is produced by joining too monosacchaarides. The boond that holdss
the tw
wo monosacccharides togetther is called a glycosidic bond.
b

Two glucose moleecules can be joined to prooduce a moleccule of maltosse [and a molecule of wateer].

A seccond disacchaaride, the com

mmon table suugar known as
a sucrose, is produced
p by combining
c glucose and fruuctose.

Polyssaccharides are
a produced by b adding moore monosacchharides to thee chain. Somee of the most important
i pollysaccharidess
are made
m of long homopolymer
h rs of glucose.. A homopolyymer is made entirely of onne monomericc unit repeateed many
timess. Three impoortant glucosee homopolym mers are distingguished by thhe details of thheir chemicall bonding pattterns.

To make
m the monoopolymer am mylose, or plannt starch, gluccose moleculees are joined by b [alpha] 1,44 linkages --juust like the
glycoosidic bond thhat joins two glucose units together in maltose.
m In thee [[alpha]] 1,44 glycosidic bond,
b the gluccose units aree
connnected to the first
f and fourthh carbons. Noote that all thee glucose units are orientedd in the samee direction. Thhis is
charaacteristic of thhe [[alpha]] [aalpha] linkagee.

Page 3 of 4
In glyycogen, or annimal starch, the
t glucose unnits are againn joined by [[aalpha]] 1,4 linnkages to prodduce long chaains, but side
chainns are linked to
t the main chhain by [alpha] 1,6 linkagees.

The third
t polysacccharide, celluulose, has its glucose
g units joined
j by [beeta] 1,4 linkagges. In the [beeta] [beta] linkkage,
alternnating glucose units are 'fliip-flopped'. Changes
C in thee bond configguration causee changes in thet final shappe and
functtion of the moolecules.

Page 4 of 4