CARBOHYDRATES

o a.k.a. SACCHARIDES *INTERNAL HEMIACETAL FORMATION – process

o (CH2O)n of ring formation
 n – number of atoms in a unit
 CH2O – hydrated carbon 2 WAYS OF FORMING A RING:
o Major energy cycle of life o Reaction of C1 & C5 via HYDROXYLATION
(PYRANOSE RING *5C & 1 O2)
FUNCTION: o Reaction of C1 & C4 (FURANOSE RING) 5
1. energy storage/generation membered ring
2. structural
3. molecular recognition CYCLIZATION
o Produces asymmetric centric carbon –
CLASSIFICATION: ANOMERIC
1. MONOSACCHARIDE – one polymer o OH & H change (interchange)
o C1 – farthest to the right (in ring)
2. OLIGOSACCHARIDE – few polymer o Can produce 2 or more anomeric configuration
3. POLYSACCHARIDE – many polymer (alpha and beta)

MONOSACCHARIDE – named by bases on the MUTAROTATION

number of carbon atoms o Alpha can be Beta and vice versa
o Change of configuration
*simplest form: TRIOSE o ALPHA – OH is below H
*more biologically important: HEXOSE & PENTOSE o BETA – OH is above H
CLASSIFICATION OF MONOSACCHARIDES WAYS TO WRITE CARBOHYDRATES:
A. ACCORDING TO THE GROUP ATTACHING TO
IT:
o FISHER PROJECTION – linear
1. ALDOSE o HAWORTH PROJECTION – ring
 Aldehyde group (CHO)
 (-ose) IMPORTANT MONOSACCHARIDES:
2. KETOSE o GLUCOSE (C6H12O6)
 Keto group (C=O)  Most common HEXOSE
 (-ulose) except FRUCTOSE  Found in STARCH, CELLULOSE &
B. ACCORDING TO THE NUMBERING GLYCOGEN
1. ALDOSE – C1 is attached to the aldehyde  Found in VEGETABLES, FRUITS, CORN
group SYRUP & HONEY
2. KETOSE – C1 closest to the keto group  Found in DISACCHARIDES, SUCROSE,
LACTOSE & MALTOSE
*ALDOSES are more biologically important
o D-GALACTOSE (C6H12O6)
STRUCTURES OF MONOSACCHARIDES:  C4 EPIMER
o ISOMERS – same formula but different structure  Obtained from Lactose; disaccharide
 An aldohexose not found free in nature
o EPIMERS – isomers with structures varying in
 Attach to glucose as lactose
one position of carbon
o FRUCTOSE (C6H12O6)
o C4 – GLUCOSE & GALACTOSE  Ketohexose/ketose
o C2 – GLUCOSE & MANNOSE  Sweetest carbohydrate
o ENANTIOMERS – isomers that are mirror  Found in fruits and honey
images of each other  Converted to glucose in the body
-- have chiral carbos that can
produce D light DERIVATIONS OF MONOSACCHARIDES:
*modified; plays important role
*natural occurring carbohydrate in D configuration o PHOSPHATE ESTERS
o DIASTEREOISOMERS – possesses more than 1  PHOSPHORYLATION OF
chiral carbon MONOSACCHARIDES
-- not mirror images  ATP, AMP, nucleic acid
Ex. D/L erythrose; D/L threose
o ANOMERS – isomers that differ in position o ACIDS & LACTONES
-- 5 or 6 carbons (ring structures)  OXIDATION OF
-- internal hemiacetal formation MONOSACCHARIDES
  Produces GLUCORONIC  Found in starch
ACID
o ALDITOLS o GLYCOGEN
 REDUCTION OF MONOSACCHARIDES  Polysaccharide found in LIVER & MUSCLE
 Produces SORBITOLS  Storage form of glucose in body
o AMINO SUGARS  Branched: formed by Glycosidic Bond:
 Sugar with amino group ALPHA-1,4 & ALPHA-1,6
 Monosaccharide with amino groups  Not found in potato
 Ex. GLUCOSAMINE – better cartilage
GLUCOSE
o High osmotic pressure
OLIGOSACCHARIDE – linked monosaccharides
o Small molecule, GLUCOGEN – semi-soluble (do
GLYCOSIDIC BOND not change osmotic pressure, ready to use when
o Links monosaccharides metabolism is acquired) GLUCOGEN ->
o Formed by removing water GLUCOSE

*DISACCHARIDE GROUP – important group
LACTOSE – formed by GLUCOSE & GALACTOSE
NAMING OLIGOSACCHARIDES:
o Non-reducing sugars first
o From left-right
o PREFIX: ALPHA or BETA
o SUFFIX: pyranose, furanose
o –cyl
o LINKAGE: (1,4) *pyranocyl, furanocyl
1 mono + 1mono = disaccharides
Ex. Glucose + glucose = Maltose
Glucose + galactose = Lactose
COMMON DISACCHARIDES:
GLUCOSE + FRUCTOSE = SUCROSE
(1,4) GLUCOSE + GLUCOSE = MALTOSE
GLUCOSE + GALACTOSE = LACTOSE
(1,4) GLUCOSE + GLUCOSE = CELLOBIOSE
(1,6) GLUCOSE + (1,4) GLUCOSE = ISOMALTOSE
STRUCTURAL:
o CELLULOSE
 Polysaccharide found in plants
 Linked by BETA-1,4 glycosidic bond
 α-glycosidase – can only break α bonds;
found in man
 β -glycosidase – can only break β bonds;
found in cows, goats, etc.
 cow’s intestinal tract has bacteria that
produce BETA glycosidase
o CHITIN – polysaccharide found in shell,
invertebrate, insect and fungi
o PEPTIDOGLYCAN –polysaccharide in the cell
wall of bacteria
o GLYCOSAMINOGLYCAN – they form the matrix
of connective tissue
MOLECULAR IDENTIFICATION:
GLYCOPROTEIN – protein linked to
sugar/carbohydrate

POLYSACCHARIDE
o Structural
o Catalyzed by enzymes
o Polymers of saccharide linked by glycosidic bond
o Storage form of sugar ex. Glycogen & starch
STORAGE:
o AMYLOSE
 Polysaccharide; storage form of sugar in
plant (starch)
 Saccharide link by ALPHA-1,4-GLYCOSILIC
BOND
 Polysaccharide arrange in linear manner
linked by ALPHA-1,4-GLYCOSIDIC BOND
 Found in potato & starch
o AMYLOPECTIN
 Polysaccharide arranged in branch manner
or structure linked by ALPHA-1,4-
GLYCOSIDIC BOND
 Branch structure ALPHA-1,6-GLYCOSIDIC
BOND
2 FORMS:
o O– LINKED – sugar is attached to protein
through SERINE/ THREONINE
o N- LINKED – sugar is attached to protein through
ASPARGINE
*ER – produce proteins
* GOLGI COMPLEX – modifies proteins
FUNCTION OF N-LINKED
o Identify cell surface (IMMUNOGLOBULIN)
o TIME CLOCK – signals for digestion (phagocytic
cells)
o INTRACELLULAR TRANSPORT SIGNAL
(labeling proteins)
FUNCTION OF O-LINKED
o Anti-freeze substance
o Increases viscosity of secretion *MUCIN*
o INTRACELLULAR TRANSPORT SIGNAL
-Rosette Go 082108 