carbohydrates (b1- foundation) Flashcards
(65 cards)
carbohydrate definition
polyhydroxyl alcohols with aldehyde or ketone groups
needs to have at least 3 n’s in (CH2O)n otherwise not classified a carbohydrate
what are the functions/biochemical significance of carbohydrates?
- Main source of energy/energy production- brain cells & RBC’s almost wholly depend on carbs as energy source
- Glycoproteins and glycolipids are components of cell membranes & receptors
- Storage form of energy (starch and glycogen are the storage forms)
- excess carbohydrate is converted to fat
- structural basis of many organisms: cellulose of plants, exoskeleton of insects, cell wall of microorganisms, mucopolysaccharides as ground substances in higher organisms
basically just all has to do with energy
what does classification of carbohydrates depend on?
on hydrolysis
on how hydrolyzed they can be
- ex. monosaccharides cannot be hydrolyzed further
what are the 4 classifications of carbohydrates? (do not confuse w/ classifications of monosaccharides!!) w/ examples of each
1. Monosaccharides: 1 unit-simple sugar
- *ex: glucose, fructose, galactose
2. Disaccharides: 2 monosaccharides
- ex: sucrose, lactose, maltose
3. Oligosaccharides: 2-10 monosaccharides
- ex: raffinose & stachyose
4. Polysaccharides: 10+ monosaccharides
- further divided into heteropoly & homopoly saccharides
- ex: glycogen, GAGs, starch, cellulose
what are the 2 further classifications of polysaccharides and what are their examples?
homopoly saccharides: long chains made up of only 1 type of sugar
- ex: glycogen, starch, cellulose
heteropoly saccharides: long chains made up of different types of sugars
- ex: GAGs, glycoproteins, proteoglycans
what are the 2 basis that monosaccharides are further classified on?
- According to functional group (aldoses & ketoses)
- According to the # of carbon atoms
monosaccharide classification based on functional group + examples
aldoses: have aldehyde group (-CHO)
- ex. glucose
ketoses: have ketone group (C=O)
- ex. fructose
monosaccharide classification according to number of carbon atoms
Trioses: 3 carbon atoms
- ex: glyceraldehyde, dihydroxyacetone
Tetroses: 4 carbon atoms
- ex. erythrose, erythrulose
Pentoses: 5 carbon atoms
- ex. ribose, ribulose
Hexoses: 6 carbon atoms
- ex. glucose, fructose
first example is the aldose sugar, second is the ketone sugar
we stop at hexose even though there are further classifications after that
glyceraldehyde, structure, and the 2 types
smallest simple sugar - reference sugar
- has 3 carbon atoms but only 1 is chiral
position of OH group on chiral (asymmetric) carbon
- if on the right → D type
- if on the left → L type
D-glyceraldehyde:
H - C = O
|
H - C - OH
|
CH2OH
L-glyceraldehyde:
H - C = O
|
OH- C - H
|
CH2OH
biochemical significance of D-Ribose
pentose (monosaccharide)
found in nucleic acid
importance: structural element of nucleic acid & coenzymes
- ex. ATP, NAD, NADP, Flavoproteins, Ribulose phosphate
dietary classification of carbohydrates (I dont think this is too high yield tho)
carbohydrates → simple & complex
simple → sugars → mono & disaccharides
complex → starches & fiber
fiber → soluble & insoluble
this I just wrote out roughly
definition of stereoisomerism
compounds with the same structural formula but different spatial orientation of groups called stereoisomers (like glucose, fructose, mannose, & galactose)
what are 2 types of carbon atoms? (chiral & penultimate)
chiral/asymmetric: 4 different atoms or groups are attached
penultimate: 2nd last carbon (next to last)
counting of carbon atoms changes based on functional group/double bond (remember the whole numbering system
most naturally occurring sugars are what type of isomer?
D isomer
sugars that have more than 1 chiral carbon are classified as D & L types based on what?
position of the OH group on penultimate (second to last) asymmetric carbon atom
- whether on the right or left
epimers vs isomers
epimers: differ in configuration around ONLY ONE carbon atom
- ex. glucose & mannose are C2 epimers
isomers: differ in configuration around 2+ carbon atoms
- ex. galactose & mannose are isomers
“D & L” isomerism / enantiomers
in structures that are mirror images of each other (enantiomers)
- OH group farther from the C=O has to be on the right to be D-isomer
- OH group farthest from the C=O has to be on the left to be L-isomer
basically penultimate carbon
think L for left
example of epimerism (mannose & galactose)
mannose → C2 epimer of glucose (H is on the right instead, OH is on the left instead at 2nd carbon)
galactose → C4 epimer of glucose (H is on the right instead of OH, OH on left instead at 4th carbon)
think that mannose has 2 n’s so its the C2 epimer, the other one is the C4 epimer
fischer projection of glucose
H – C = O
|
H – C – OH
|
HO – C – H
|
H – C – OH
|
H – C – OH
|
CH2OH
1st & 5th are achiral b/c double bond & multiple H’s attached
what is an anomeric carbon? UQ
in water, glucose folds into a ring (OH group on carbon 5 reacts w/ carbonyl group) so use haworth projection (the ring ones)
anomeric carbon: carbon that was part of the carbonyl group (the aldehyde or ketone) before the ring formed
- after ring formation, becomes a new chiral center (this is v. imp!)
difference in ketoses & aldoses and how that affects the anomeric carbon + examples
in aldoses (like glucose) → carbonyl group (double bond to the C) is on C-1 so C-1 becomes the new anomeric carbon → becomes 6 membered ring
- ex: pyranose
in ketoses (like fructose) → carbonyl group is on C-2 so C-2 becomes the new anomeric carbon → becomes 5 membered ring
- ex: furanose
what are anomers and what are the 2 types?
anomers: isomers that differ in configuration around the anomeric carbon atom
α-anomers: OH is facing down in the haworth structure
- think a for away so the group is going away
β-anomers: OH is facing up in the haworth structure
- b for birds and birds fly so going up
example of α-D-glucose and β-D-glucose
what is optical isomerism?
chiral carbon (isomers only exist in chiral compounds) has the ability to rotate plane polarized light to the left or right
L (Levorotatory) or (-): means rotates to the left
D (dextrorotatory) or (+): means rotates to the right
NOT THE SAME AS D & L ISOMERISM WHICH ARE ENANTIOMERS & BASED ON HOW IT LOOKS NOT HOW IT ROTATES LIGHT
sugars can be designated either D (-), D (+), L (-), or L (+)
list the 4 types of isomerisms we discussed
- D & L isomerism (enantiomers)
- Epimers
- Anomers
- Optical Isomerism