Carbohydrates and metabolism Flashcards
generic form of common CHO
Cn(H20)n - they are carbon hydrates
- some may contains N, P or S
biochemical description of CHO
polyhydroxyl compounds that carry an aldehyde or ketone group, or substances that yield such compounds upon hydrolysis
three classes of CHO
- monosaccharides
- oligosaccharides
- polysaccharides
what are monosaccharides
simple sugars
e.g D-glucose, D-fructose
what are oligosaccharides
short-chain sugar units of 2-10 or 20
e.g fructans
what are polysaccharides
> 10 or 20 sugar units, usually a bioassembly and so not found on their own
e.g starch and cellulose
what characterises oligosaccharides and polysaccharides
glycosidic linkages
significance of CHO
- must abundant biomolecule in the world (structural & storage CHO)
- Supplies energy for animal & human nutrition (dietary staple)
- play an important role in human metabolism and health (fibre)
- wide industrial uses (oils, textures, paper & pharmaceuticals)
- green polymers (bioplastic, thermoplastc starch)
- films for wound dressing (chitosan films)
- biofules (cellulose and starch)
name the common monosaccharides
- Ara
- Fru
- Fuc
arabinose
fructose
fucose
name the common monosaccharides
- Gal
- Glc
- Man
Galactose
glucose
mannose
name the common monosaccharides
- Rib
- Rha
- Xyl
ribose
rhamnose
xylose
name the common monosaccharides
- GlcUA
- GalN
- GalNac
- GlcNac
- glucuronic acid
- galactosamine
- N-acteylgalactosamine
- N-actetylglucosamine
what does glucose need bc it is a reducing sugar
active carbonyl group
what happens to D-glucose in water
a mixture of alpha, beta and open chains form
four most common hexoses
glucose, mannose, galactose and fructose
what shape are pyrnaose rings
they are NOT flat as in Haworth projections
- occur in a variety of shapes
- chair is most common conformation,
- boat conformation
what are the two possible chair forms of glucose pyranose
4C1 and 1C4
which is the most stable chair form in sugars
4C1 because the bulk C-6 group is in equatorial locations
what are the differnet location descrptors
equatorial and axial
what are sugars linked by
O-glycosidic bonds
where is sucrose hydrolysed and what to
in the gut, to fructose and glucose
is frcutose a reducing sugar
no, becuase the C group is in the glycosidic linkage. But once hydrolysed it produced fructose and glucose which are reducing
solution used for testing if sugar is reducing
Fehling’s
what is sucrose used to make
sucralose - artificial sweetner AKA splenda
what is Splenda
sucralose, artifical sweetner
how is sucralose made
chlorine is added to the C4 of Glc and to C1 and C6 of the Fru of a sucrose molecule
properties of Splenda
- very stable
- resistant to heat treatment
- not hydrolysed to the gut
- thousands times sweetner than sucrose
- zero calories bc not hydrolysed
is maltose a reducing sugar
yes, aldehyde group is free to react with oxidants
where is maltose found
- rarely found in nature
- forms from hydrolysis of starch in human gut
- found in malted grains e.g barley
is lactose a reducing sugar
yes
where is lactose found
milk
what causes lactose intolerance
deficiency in lactase.
Not common in areas where dairy is requent consumed
methods of overcoming lactose intolerance
use of reduced lactose milk
addition of lactase to products - expensive
Trehalose
- oligosaccharide
- found in shrimp, fungi, yeast and blood of insects
- high water retenton useful for anhydrobiosis (tide)
- means that plants and invertebrate animals can withstand dessication (Removal of water)
Raffinose
- oligosaccharide
- found inn foods like cabbage, beans and brussel sprouts
- made up of galactose, glucose and fructose
- not digested in upper gut
- fermented in large intestine
- fermentation produces SCFA and gas (flatulence)
Satchyose
- oligosacharide
- naturally found in vegetables e.g beans and legumes
- used as a bulk sweetner
- not digested by upper gut in humans = no calories
- similar to raffinose but different strucure bc of one extra galactose
fructo-oligosaccharide
- oligosaccharide
- storage CHO in chicory root and jerusalem artichoke
- main source is cereals due to large consumption
- could be argued as polysaccharide bc 2-60 sugar units
- studied for pre-biotic effects, promotes growth of bifidobacteria
DP
degree of polymerisation
e.g DP >40 = polysaccharide
what controls chain conformaton of polysaccharide
chain geometry
- from flexible disordered coil through to packed linear arrays and helices
- 1,4 and/or 1,6 glycosidic bonds
different types of glycosidic bonds and conformation
- 1,4 diequatorial
- 1,4 diaxial
- 1,4 Ax-Eq
1,4 diequatorial
- linkage patterns are packed giving ribbon like strcuture packed in to tough fibriliar assemblies
- equatorial link is the 1,4 coming in and out of the ribbon structure
- ribbon strcutures themselves are held together with hydrogen bonds
1,4 diaxial
- ribbon like but hghly buckled structures that produce cavaties
- counter ions (calcium) sit in the cavaties and interact to hold structure together
1,4 Ax-Eq
- bonds of sugar units are not parallel
- twist in a chain
- mixture of axial and equatorial bonds
- helical structure
what is the main supplier of exogenous glucose in humans
starch
what us starch in plants
CHO reserve; tubers and seed endorsperm
size of starch granules
variable
1-100 micrometers
what is starch made from
2 glucose polymers
- amylopectin
-amylose
and some lipid, and protein for biosynthesis
dominate glucose polymer in starch
Amylopectin (70-90%)
Amylose is 10-30%
strcuture of amylose
- linear chains of alpha-D-glucopyranosyl units
- 1,4 glycosidic bonds
- low levels of branching
- likes to form single helix, stabilised by H bonds
- hydrophobic inner surface
- starch-lipid complexes arent easily digested in gut
structure of amylopectin
- very large molecle
- chains of alpha-D-glucopyranosyl units
- molecular weight of 10^6 -10^8
- 4-5% of Glc units are involved in 1,6 glycosidic bonds
- branched polymer
what are the essential features of the cluster model of starch
- A chains on the outside
- B chains on the inside
- reducing end inside
organisation of amorphous and crystalline regions of starch
amorphous regions are more readily attacked by amylase.
alternating strips of amophous and crystaline regions
difference between A types and B types of tarch
A are more tighly packed and bind less waer than B
what forms packed double helices
short chains of amylopectin (6 units)
- some helices will pack into crystalline lamella or crystalites
glycogen structure
- highly branched with alpha-D-glucopyranosyl units
- glycosidic linksages at both 1,4 and 1,4
- similar to amylopectin but more highly branched
- built on a protein backbone
- glycogen granules are 0.1 microm in hepatocytes
size of glycogen granules in hepatocytes
0.1microm
celluose structure
- glucan polymer, contains only Glc
- consists of D-glucose units linked in Beta-1,4 configuration
- forms a packed ribbon-like structure
- individual parallel chains held together by H bonds
- msot animals cannot digest Beta-1,4 linkages
- water insoluble
what does mixed 1,3 1,4 beta-D-glucan linkages show
fluorescence
where are mixed linkage beta glucans found
endosperm cell walls of cerelas e.g barley and oats
why is there interest in mixed linage beta glucans
- 1,3 links make it water soluble
- water solubilty and high molecular weight = viscocsity
- reduces blood glucose
- reduces cholesterol by lowering LDL
- beta glucan increase viscosity in the gut
what are pectins
- linear polymers of alpha-D-galacturonic acid linked by 1,4 bonds,
- a proprtion of COOH esterified with methanol
- molecular weight >100K
sugars involved in the main or branched chain of pecti
L-Rha, D-Glc, L-Ara
what is apple pectin
rhamnogalacturonan with xylose and arabinogalactan side chains
where are pectins found
primary cell wall and middle lamella of plants