Carbohydrates Flashcards
Formula of carbohydrates .
Cn(H2O)n
What are the hydrates of carbon
Sacharides
Monosaccharides, disaccharide- 1unit ,2unis
Oligosaccharides- few units
Polysaccharide- 100-1000s units
Triose, Tetrose, pentose- 3C, 4C, 5C
What are the functions of carbohydrates
Energy transport and storage
Structural function- bacterial cell wall
Informative activity- cell and protein signalling
What are the two major carbohydrates families?
Aldoses and ketoses
What are the derivatives of main carbohydrates ?
Aldoses - D-glyceraldehyde
Ketoses- Dihydroxyacetone
Characteristics of carbohydrates
1- asymmetric (chiral) carbons
2- AA are usually L, however carbohydrates are D
3-carbohydrates are optically active- rotate the monochromatic plane polarized light in opposite directions
4-many exists in cyclic forms. They carbonyl groups have a tendency to react reversibly to alcohols forming a hemiketal, pr hemiacetal
Conditions of cyclic carbohydrates ?
1-Must have a carbonyl group and one or more alcoholic hydroxyls
2-steric ? 4 or less carbon cant form rings because they are unstable, so the carbohydrates must have or more carbons
Characteristics of cyclic compounds
1- reversible
2- more stable
3-create an additional chiral centre
What are the two structure glucose can form?
a-D-Glucopyranose / A-anomers - OH on C1 is same side of C6
b-D-Glucopyranose/ B-anomer- OH on C1 is opp side of C6
These two structures are drawn in HAWARTH diagram
-And these two structures are called anomers , bcz these isomers only differ at hemiketal or hemiacetal C
-they are both planar but not entirely bcz they can both exist in chair and boat form
Draw the two structures
Why are there two cyclic structures of glucose?
As we said earlier, cyclic structures create an extra chiral centre, in glucose these chiral centre can be created in two different ways on C1
What is pyranose and why is it favoured
Pyranose are 6 membered sugar-rings, they are more favoured due to more numbers of carbons makes it more stable over the 5 membered ring.
It also contains the ring pyran
Can sugars exist as Fischer structures?
Yes they can
- these are chain structures that are correct / stable for C3 to C4however, compounds with higher number of Cs , cyclic structure is more stable
- in aqueous solution (water)- a,b and fisher exist in equilibrium
- a and b interconvert through little amount of chain structure
Which structure of glucose is most stable in water?
B > a>chain(fischer)
64>36>0.01%
What is mutarotation? And how is it measured?
It is the inter conversion between a anomer and b anomer through trace amounts of chain structure
It can be measured using plane-polarized light.
How can mutarotations be measured using plane-polarized light
Pure A-anomer rotates light at +112
Pure b-anomer rotates light at +19
A mixture of these two rotates light at
0.36x(112)+0.64x(12)=+53
Diving deeper into the glucose anomers partially planar ability ,recall why they are not completely planar?
Because each of them can exist in 2 conformation
Chair and boat confirmation
Which of the conformation of glucose (chair or boat )is more stable or preferred?
Chair conformation is more preferred be cause it is less crowding/hindrance of bulkier groups around the ring
What are the two positions of groups on these conformation?
E- equatorial- group-is in plane to the planar part of ring
A- axial - group is perpendicular to planar part of ring
Which of the positions ( E or A) is more stabLe and why?
Equatorial because less steric is hindrance of the groups around the ring
Recall that in aq solutions , the most abundant structure of glucose was in B anomers, why is this so?
Yes, it was 64%
This is because only the b anomer can put all of its bulkier group (oh) in equatorial positions.
Draw the boat and chair conformation of a anomer