BIOCHM E2 C7
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NAME 5 CLASSES OF Carbohydrates
- The Sugar Code
----------- are the most abundant biomolecule in nature
Sugars with an aldehyde functional group are ------
Sugars with an ------ functional group are ketoses
------------------ or simple sugars, are polyhydroxy
aldehydes or ketones
ALDOSE OR KETOSE?
ALDOSE OR KETOSE?
WHAT'S THE DIFFERENCE BETWEEN ALDOSE AND KETOSE?
Carbohydrates are precursors for other biomolecules. EXPLAIN WHY/HOW.
THEY CAN CONVERT TO OTHER PRODUCTS. PROTEINS---> SUGARS
Most abundent carbihydrates in living cells are:
---- & -----.
hexoses and pentoses.
Trioses OR hexoses...WHICH ONE IS FOUND IN DNA?
T OR F ?
Class names often combine information about carbon number and functional group
WHAT IS THIS? MUST DRAW FOT THE TEST!!
- COUNT THE CHIRAL CENTER. THERE'S 5.
WHAT DOES D-RIBOSE LOOK LIKE?
HOW MANY CHIRAL CARBONS?
- 5 CHIRAL CARBONS.
- MUST DRAW FOR TEST!!!!
WHAT IS THIS?
- ALDEHYDE FORMATION.
- FOUND ON GLYCERALDEHYDE.
HOW MANY CHIRAL CARBONS IN D-GLUCOSE?
MUST DRAW FOR TEST !!!!
WHAT IS IT? MUST DRAW FOR TEST!!!!
T OR F?
An increase in the number of chiral carbons increases the number of possible
"2n"...WHAT DOES THE "n" MEAN?
"n" IS THE NUMBER OF CHIRAL CARBONS.
4 chiral centers = ? isomers
WHAT'S THE DIFFERENCE BETWEEN A ALDOSE AND KETOSE?
- A chain-form monosaccharide that has a carbonyl group (C=O) on an end carbon forming an aldehyde group (-CHO) is classified as an aldose.
- When the carbonyl group is on an inner atom forming a ketone, it is classified as a ketose.
Almost all naturally occurring monosaccharides are WHAT FORM? D OR L?
In optical isomers, the ------ carbon is the asymmetric
carbon farthest from the carbonyl carbon
- REFERENCE CARBON.
WHAT THE HELL IS THIS? MUST DRAW FOR TEST!!!!
MUST BE ABLE TO DRAW D-GALACTOSE FOR THE TEST!!!
Almost all naturally occurring monosaccharides
can be considered to be derived from D-glyceraldehyde
or ------------- ------------------.
------------ are stereoisomers that are mirror
images (D vs. L)
------------- stereoisomers that are not enantiomers
Diastereomers that differ at a single chiral carbon are ---------- (e.g., D-riboseand D-arabinose) See arrows.
T OR F?
Arabinose is an epimer of
ribose (or ribose is an epimer of arabinose).
Sugars with four or more carbons exist primarily in WHAT FORM?
cyclic forms (ring forms)
Ring formation occurs because aldehyde and ketone groups react reversibly with
hydroxyl groups in an aqueous solution to form
------- & ---------.
hemiacetals and hemiketals
hemiacetals and hemiketals.
HOW ARE THEY FORMED?
- Ring formation occurs because aldehyde and ketone groups react reversibly with
- hydroxyl groups in an aqueous solution.
HOW IS A HEMIACETAL FORMED?
- RING STRUCTURE FORMED BY ALDEHYDE AND ALCOHOL IN AQUEOUS SOLUTION.
HOW IS A HEMIKETAL FORMED?
- RING STRUCTURE FORMED BY KETONE AND ALCOHOL IN AQUEOUS SOLUTION.
Two possible diastereomers that form because of cyclization are called --------.
two possible diastereomers that
form because of cyclization are called anomers.
- Hydroxyl (-OH) group on hemiacetal
- occurs on carbon 1 and can be in the up position (above ring) or down position (below ring).
In the D-sugar form, when the anomer
hydroxyl is up it gives a -- ------- FORM.
- b-D-anomeric form
- (left in Fischer projection) .
In the D-sugar form, when the anomerhydroxyl is up it gives a -- ------- FORM.
- a-D-anomeric form
- (left in Fischer projection) .
Haworth Structure of the A-D-Glucose.
1. IS THE -OH ON THE FIRST CARBON DOWN OR UP? MUST DRAW FOR TEST !!!!
2. WHAT IS IT'S FORMAL NAME IN THE HAWORTH STRUCTURE FORM?
- a-D-glucopyranose (6 SIDED RING)
Haworth Structure of the B-D-Glucose....IS THE -OH ON THE FIRST CARBON DOWN OR UP?
MUST DRAW FOR TEST!!
- UP. REMEMBER BOAT.
Five-membered rings are called -------.
Six-membered rings are------
Cyclic form of fructose is ----------- ,
while glucose in the pyranose form
BE ABLE TO DRAW D-FRUCTOSE IN A FISHER FORM.
MUST BE ABLE TO THE ALPHA & BETA FORM FROM THIS:
WHAT IS THE "BUSINESS END" OF A MONOSACCHARIDE?
- ANOMERIC END...REACTIVE...CARBOXYL OR ALDEHYDE....FORMS PRODUCTS.
This spontaneous process,--------- produces
an equilibrium mixture of a- and b-forms
in both furanose and pyranos ring
- Open chain form can participate in redox reactions-Bendicts test.
3 IMPORTANT MONOSACCHARIDES ARE NOTED IN LECTURE. GIVE THE HAWORTH FORM NAME OF THEM.
- a-D-glucopyranose (GLUCOSE AKA DEXTROSE)
- b-D-fructofuranose (FRUCTOSE)
- a-D-galactopyranose ( GALACTOSE)
The primary fuel for living cells.
Preferred energy source for brain cells and cells without mitochondria (erythrocytes).
We get a ton of it from HFCS (high fructose corn syrup and break down of starch).
WHAT THE HELL IS IT?
GLUCOSE (D-GLUCOSE) (DEXTROSE)
HFCS—high fructose corn syrup—processed mixture of ------- & --------used as as a
sweetener. (combine to give ratios similar to table sugar—sucrose).
glucose and fructose
On a per gram basis, it is twice as sweet as sucrose, therefore it is often used as
a sweetening agent in processed food
-----------can interconvert glucose and galactose
--------------- a genetic disorder resulting from a missing enzyme in galactose
-------necessary to synthesize a variety of important biomolecules (found in milk in
lactose). Important biomolecules include: lactose, glycolipids, phospholipids, and glycoproteins
Reaction and Modification of Monosaccharides the
---- & ------ groups can undergo several chemical reactions.
carbonyl and hydroxyl
Reaction and Modification of Monosaccharides
NAME THE TOP 5
- glycoside formation,
- glycosylation reactions
T OR F?
All monosaccharides are reducing sugars and some di and polysaccharides
are as well as long as anomeric carbon not in fixed linkage
Sugars that can reduce another species (they become oxidized in the process) such as
Cu+2 to Cu+1 (Benedict’stest) are called -------?
monosaccharides may readily undergo several -------- reactions in the presence of metal ions or
OXIDATION (GAIN OXYGEN)
Oxidation of the aldehyde group yields ----- -----.
Oxidation of the terminal CH2OH
group yields ----- -----.
Oxidation of both the aldehyde and the CH2OH groups yields ----- ------.
THE OXIDATION PRODUCTS OF GLUCOSE INCLUDE WHAT?
- aldonic (OX OF -CHO)
- aldaric (OX OF -CH2OH)
- uronic acid (OX OF BOTH)
2 MAIN SUGARS IN HFCS
(high fructose corn syrup)
BREAK DOWN STARCH....GET GULCOSE AND MIX WITH FRUCTOSE....TA DA HFCS!
----- can be produced if the carbonyl groups of aldonic or uronic acids react with an OH group in the same molecule.
Lactones are readily produced in nature, for example
- L-ascorbic acid
- (vitamin C) a powerful reducing agent that protects cells from reactive oxygen and
- nitrogen species.
---------- are produced by the reduction of aldehyde and ketone groups of monosaccharides
ALDITOLS (Sugar alcohols)
WHAT THE DIFFERENCE BETWEEN ALDITOLS AND ALDONIC ?
- ALDITOLS....reduction of aldehyde and ketone GROUPS.
- ALDARIC...OX OF BOTH aldehyde and ketone
Sugar alcohols (alditols) are produced by the ------ of aldehyde and ketone groups of monosaccharides
EXAMPLE OF ALDITOL (SUGAR ALCOHOL) USED IN FOOD AND PHARMACEUTICALS.
SORBITOL. HELPS PREVENT MOISTURE LOSS.
REDUX OR OX?
Reduction (gain hydrogens)
D-glucose incubated in an alkaline (STRONG BASE) solution for several hours produces two isomers: D-mannose
and D-fructose...KNOWN AS WHAT?
- 2 MONOSACCHARIDES, DIFFERENT BY ON CHIRAL CARBON.
T OR F ?
The transformation of glucose to fructose is an aldose-ketose interconversion
form between oligosaccharides and the side chain amide nitrogen of certain
- BONDS TO "N" OF THE NH3.
------ Glycosidic linkages attach glycans to
the side chain hydroxyl of serine or threonine residues, or the hydroxyl oxygens of
POST TRANSLATION MODIFICATIONS ARE A RESULT OF WHAT?
- Glycosylation Reactions attach
- sugars or glycans (sugar polymers) to proteins or
- lipids—i.e. post translation modifications
Catalyzed by -------- ---------- glycosidic
bonds are formed between anomeric
carbons in certain glycans and
oxygen or nitrogen of other types of molecules, resulting in N- or O-glycosidic bonds
IS THIS GLUCOSEAMINE?
- NO. Galactoseamine. YOU MUST KNOW GLUCOSEAMINE FOR TEST! FLIP -OH ON CARBON 4 DOWN.
WHAT 2 AMINO SUGARS ARE THE MOST COMMON AND OFTEN ATTACHED TO PROTEINS OR LIPIDS?
- and D-galactosamine
DEFINE Deoxy Sugars.
- Monosaccharides that have an –OH replaced by an –H or –CH3.
- EX: Fucose & 2-deoxy-D-ribose
NAME 2 MONOSACCHARIDE DERIVATIVE GROUPS
DEOXY AND AMINO SUGARS
In polysaccharides, large numbers of monosaccharides are linked together through ------ ----- OR ------ ------.
- acetal linkages or glycosidic linkages.
- BOTH MEAN THE SAME THING. ACETAL LINKAGE IS THE FORMAL WAY OF STATING IT.
Naming of glycosides specifies the sugar component,
Acetals of glucose and fructose are ---- & ------.
- glucoside and fructoside.
- REMEMBER THAT GLYCOSIDIC LINKAGE AND ACETAL LINKAGES ARE THE SAME THING.
If an acetal linkage is formed between the hemiacetal
hydroxyl of one monosaccharide and the hydroxyl of another, this forms a -------.
THE BLUE BOX IS AN EXAMPLE OF WHAT?
- GLYCOSIDIC LINKAGE.
- Acetal of glucose ....glucoside.
In ----------, large numbers of monosaccharides
are linked together through acetal
linkages or glycosidic linkages
--------- --------: hemiacetals and hemiketals
react with alcohols to form the corresponding acetal and ketal
Glycoside Formation- hemiacetals and hemiketals
react with alcohols to form the corresponding ------ & -------.
acetal and ketal
When the cyclic hemiacetal or hemiketal form
of the monosaccharide reacts with an alcohol, the new linkage is a--------- ---- AND THE COMPOUND IS A ----------.
glycosidic linkage and the compound a glycoside
linked by a glycosidic bond IS CALLED WHAT?
GLYCOSIDIC BONDS CCAN OCCUR AT WHAT CARBON POSITIONS?
- ALL OF THEM! KNOW THE CARBON POSITIONS!!
LABEL AND IDENTIFY THIS. MUST KNOW FOR TEST!
WHAT TYPE OF LINKAGE?
WHY IS LACTOSE A REDUCING SUGAR?
BECAUSE IT HAS THE ANOMERIC CARBON THAT CAN INTERACT WITH OTHERS. THE -OH GROUP THAT DETERMINES IF IT'S ALPHA OR BETA.
T OR F?
WHEN UTILIZING DISACCHARIDE NOMACLATURE, STRUCTURAL IDENTIFICATION AND BOND LINKAGE IDENTIFICATION ARE DONE TWO DIFFERENT/OPPOSITE WAYS.
THE alpha(1,4) linkage between two molecules of glucose...DEFINE THE LINKAGE TYPE
GLYCOSIDIC (OR ACETAL) LINKAGE
-------- is an intermediate product of starch hydrolysis.
Does not exist freely in nature but readily found in junk food
WHAT THE HELL IS THIS?
One molecule of galactose linked to one molecule of glucose FORMS WHAT?
two molecules of glucose LINKED TOGTHER FORM WHAT?
MALTOSE (MALT SUGAR)
--------- is a degradation product of cellulose (i.e. wood and paper) is composed of two molecules of glucose linked with a b(1,4) glycosidic bond
Do not confuse with lactose!!!!
- MUST RECGONIZE FOR TEST!!!!
DEFINE THE ENTITE STRUCTURE AND THE 2 SUBUNITS. MUST KNOW FOR TEST!!
- Cellobiose is composed of two molecules of glucose linked with a b(1,4) glycosidic bond.
MUST KNOW THIS STRUCTURE:
- Sucrose is common table sugar (cane or beet
- sugar) produced in the leaves and stems of plants.
One molecule of glucose linked to one molecule of fructose, linked by an a,b(1,2) glycosidic bond.
Glycosidic bond occurs between both anomeric carbons.
Nonreducing sugar... Both anomeric carbons in bond.
One molecule of glucose linked to one molecule of fructose, linked by an a,b(1,2) glycosidic bond...WHAT AM I?
- SUCROSE. MUST KNOW FOR TEST!!
WHY IS LINKAGE NAMED DIFFERENTLY ON SUCROSE?
BECAUSE BOTH ANOMERIC CARBONS ARE LINKED.
DEFINE UNIT, SUBUNITS AND NUMBER CARBONS.
Polysaccharides can be ---- OR ------.
linear or branched
Polysaccharides have been divided into two classes. NAME THEM
homoglycans and heteroglycans
DEFINE HOMOGLYCAN POLYSACCHARIDES
- Have one type of monosaccharide and found in starch, glycogen, cellulose, and chitin.
- Starch and glycogen are energy storage molecules while chitin and cellulose are structural—
WHAT 2 POLYSACCHARIDES WOULD YOU FIND IN FISH WRAPED IN PAPER?
CHITIN (FISH) & CELLULOSE (PAPER)
energy reservoir of plant cells and a significant source of carbohydrate in the
Two polysaccharides occur together in starch. NAME THEM
AMYLOSE & AMYLOPECTIN
----------- is composed of long, unbranched
chains of D-glucose with a(1,4) linkages between them.
------------- typically contains thousands of glucose monomers and a molecular weight from
----------- are branched polymer containing both a(1,6) and a(1,4) linkages. Branch points occur every 20 to 25 residues
In amylopectin, branch point every 20-25 residue on WHAT position?
--------is the carbohydrate storage molecule in vertebrates found in greatest abundance in
the liver and muscle cells
Up to 8–10% of the wet weight of liver cells and 2–3% in muscle cells
GLYCOGEN VS AMYLOPECTIN...WHAT HAS MORE BRANCH POINTS?
More compact and easily mobilized than other polysaccharides—used for quick “energy
source” in the human body but can be depleted rapidly...WHAT IS IT?
-------- is a polymer of D-glucopyranosides
linked by BETA (1,4) glycosidic bonds.
- IT'S A BRUNCH OF CELLOBIOSE BONDED TOGTHER VIA B(1,4) GLYCOSIDIC BONDS. AND CELLOBIOSE IS JUST 2 GLUCOSE.
Pairs of unbranched cellulose molecules (----- glucose units each) are held together by------
bonding to form sheetlike strips, or --------.
Major types: N- and O-linked glycosaminoglycans (glycans), glycan components of glycolipids, and GPI (glycosylphosphatidylinositol)
anchors...HOMOGLYCAN OR HETEROGLYCAN?
- High molecular weight carbohydrate polymers that contain more than one type of monosaccharide
Found on bacteria, virus can be used to attach to host cells.
Binding of virus and bacteria to cells (lungs, etc.) -------- are proteins that recognize unique carbohydrate sequences on cells.
An oligosaccharide (from the Greek oligos, a few, and sacchar, sugar) is a saccharide polymer containing a small number (typically two to ten) of component sugars, also known as simple sugars (monosaccharides).
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