Lecture 11-12 Carbohydrates I & II Flashcards
List the 6 mono saccharides?
Glucose Fructose Galactose Mannose Ribose Deoxyribose
The bad guys, the aldehydes, reacting with proteins is where the trouble lies, what is this reaction called? 1 of the 2 bad processes discussed.
glycation
Other than glycation. The other Culprit of destroying proteins is called what?
oxidation
What is a ketose and an aldose?
A sugar with: 2 R groups off of Carbonyl 1 R group and a H off of the Carbonyl.
extra credit As proteins become glycated they become larger and less flexible, as well as yellow and brown *the Maillard rxn” this is the reason for what Endproducts?
AGE’s Advanced Glycation Endproducts -
Another name for carbohydrate?
saccaharide
list the 3, 4, 5, 6, 7 carbon sugars?
triose, Tetraose, Pentose, hexose, heptose.
Isomers are?
two molecules same molecular formula, with a different arrangement of Atoms.
Which isomers differ in the order of attachment of atoms?
Constitutional isomers - large difference, in connection.
What isomers have the same order but the spatial arrangement differs?
Stereoisomers - differ rotationally
what are the 2 major types of Stereoisomers?
Enantiomers and diastereomers
What are two specific types of diastereomers?
epimers and anomers
What are Enantiomers? diastereomers?
-Non superimposable mirror images - differ at all C -not mirror images differing rotationally at more than one C but not all
epimers? anomers?
both are diasteromers -differ only at one C -formed by a ring closure and differ at a new asymmetric carbon
Memorize! Your 2 aldose-ketose pairs that are constitutional isomers?
- glyceraldehyde & dihydroxyacetone 2. Glucose & Fructose
Most human sugars in our bodies are what kind of sugar D or L?
D sugars
MUST KNOW 2 examples of Epimers?
glucose /Mannose glucose/galactose
What are mannose and Galactose?
diasteromers
Why is the cyclical form of sugars dominant vs being in a open chain?
B/c the carbonyl group is masked and not there. so its less reactive when in cyclical form
So when a ring closes, what type of carbon is formed?
an anomeric Carbon is formed?
Which carbon becomes the anomeric carbon?
The carbonyl Carbon, (**** it will be the carbon between 2 oxygens, b/c the OH attacked the Carbonyl)
what are the two bond formations (orientations in space, up/down) that can form from a ring formation? (aka 2 anomeric formations)
Alpha or Beta form?
Alpha goes UP or DOWN? Beta?
fish (alpha) swim down, Beta Birds fly up
must have memorized what 2 trioses? which is aldehyde and which is ketone? should be easy
D-glyceraldehyde & Dihydroxyacetone
must have memorized 1 pentose? aldehyde or ketone?
D- Ribose Aldehyde
Must have memorized what 4 hexoses? Which are Aldehydes and Ketones?
Fructose (only Ketone) Glucose Mannose Galactose
Hexoses that are aldehydes form what rings?
Pyran rings, 6 membered sugar rings = Pyranose, with Oxygen in the ring. B/c OH on C5, attacks the C=O which is C1 (being an aldehyde)
Which sugar open chains form Pyran rings?
Glucose, Mannose, Galactose and other 6 C-aldoses
Hexoses that are ketones form what rings?
Furan rings, 5 membered sugar rings = Furanose, with Oxygen in the ring b/c OH on C5 attacks C=O which is C2 (being a ketone)
should some glucose be found in the urine?
No
Fehling’s Reaction tests for what type of sugar?
a Reducing Sugar!
What is a reducing sugar? Good or bad
any sugar that has a free anomeric form, which means its cyclic form opened to a chain form.
What is mutarotation?
A cyclic form or chain can be changing back and forth from one structure to the other. So the interesting thing here is that in straight chain form of glucose you have an aldehyde. this is bad, it’s a glycating agent. Which can render proteins ineffective
Glycosylation is not the same as _______ but is commonly used in our book and common writings?
Glycation
Glycation is ?
When an amino group on the protein backbone is reacting with an aldehyde sugar form instead of with its proper peptide bond, and you get a glycated protein that usually functions differently
in diabetics, their glycated Hemoglobin does bind Oxygen the same, but it alters normal biochemical function b/c it remains in circulation longer.
good for us to know. and shows applicability and future needed knowledge. we will see this again.
Name for cyclic glucose? (2 anomers)
B - D - Glucopyranose and a-D-Glucopyranose
Name for the bond between 2 saccharides?
O - glycosidic bonds O for oligosaccgharides
Just to clarify and distinguish… will need to know in near future but maybe not for this test…. N glycosidic bonds are what binds what other important biological molecule??
Sugars with Nitrogenous bases, like with Ribose and nucleosides, in RNA.
Monosaccharides are joined by glycosidic bonds to what 3 functional groups?
Alcohols Amines Phosphates
MEMORIZE, what makes it a glycosidic bond? what must be a part of the bond?
THE ANOMERIC CARBON, (which was the C of the C=O)
MEMORIZE How do you locate the Anomeric Carbon?
IT will have a bond to 2 separate Oxygens, (so it must be between 2 oxygens)***
MEMORIZE What are your 3 disaccharides?
Lactose, Maltose, Sucrose
MEMORIZE What are the 2 monosaccharides that form Lactose, and what is the linkage between them?
Glucose/Galactose B1,4= Lactose
MEMORIZE What are the 2 monosaccharides that form Sucrose, and what is the linkage between them?
Glucose/Fructose a1B2 = Sucrose
MEMORIZE What are the 2 monosaccharides that form Maltose, and what is the linkage between them?
Glucose/Glucose a1,4 = maltose
What is Antigenic when it comes to functional groups and macromoles? and what does this mean?
first, it simply means that it will act as an antigen or toxin/foreign body that stimulates an immune response. It’s the Carbonyl of Aldehydes and Ketones that this is so, and is due to inbalance of straight chain carbohydrates.
To be a reducing sugar? Must the sugar be in a ring or chain? is Sucrose Reducing?
In a ring, the anomeric carbons are in glycosidic bonds, (as in sucrose) so you do not have a Carbonyl group and therefore not a reducing sugar. Chains are where you see a reducing sugar.
Plants and animals store energy in what molecule respectively? What is the very basic difference between the 2 molecules?
Starch and glycogen respectively glycogen is highly branched and starch is not.
What has a B1-4 linkage b/w glucose/glucose but cannot be broken down by animals?
Cellulose? lactose is B1-4, but between gluc/galactose and Maltose is gluc/gluc but A1-4
When you hear the word Proteoglycan, you should think of?
Cartiliage, CT and blood vessels
When you hear glycoproteins, think?
hormones and blood protein
What are mucins?
Protein with sugars on them (100’s of them), attach to membranes, from mucous membranes.
Too build big molecules from sugars, what must be done?
The sugar must be excited by adding a UDP (uridine diphosphate) this excited states promotes a chemical reaction that creates larger macromolecules (ie glycogen from glucose, or glycoprots and glycolipids)
in the liver, biotransformation occurs, that remove wastes, wastes like billirubin (UDP glucoronate), or like char on hamburgers or other wastes. How do you think this occurs?
Sugars are added to them, and this makes them more water soluable and therefore can be removed from the body.
In glycosylating proteins (giving purpose to a protein macromolecule) there is N and O glycosylation. What are these, and why called N and O glycosylation? note This is not N glycosidic bonding
N glycosylation is attaching the sugar to the R group of Asn. O glycosylation is attaching the sugar to the R group of Ser.
SUGARS, LIKE TO BIND _ _ _ _ _ _ ?!!!!! TQ TQ
WATER! (spit is watery and slimy, sugar/water complex) mucins
TQ
What are the massive repeating sticks of 100’s of linked disaccarides attached to proteoglycans called?
glycoaminoglycans
TQ - know that chondrotin sulfate, keratan sulfate, dermatan sulfate, heparan sulfate, and hyaluranate are what?
proteoglycans - shaped like a bottle brush.
