BIOCHM E2 C7

NAME 5 CLASSES OF Carbohydrates

Monosaccharides

----------- 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.

Most abundent carbihydrates in living cells are:
---- & -----.

Trioses OR hexoses...WHICH ONE IS FOUND IN DNA?

T OR F ?

WHAT IS THIS? MUST DRAW FOT THE TEST!!

WHAT DOES D-RIBOSE LOOK LIKE?
HOW MANY CHIRAL CARBONS?

WHAT IS THIS?

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
optical isomers
True False

"2ⁿ"...WHAT DOES THE "n" MEAN?

4 chiral centers = ? isomers

WHAT'S THE DIFFERENCE BETWEEN A ALDOSE AND 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

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).
True False

Sugars with four or more carbons exist primarily in WHAT FORM?

Ring formation occurs because aldehyde and ketone groups react reversibly with
hydroxyl groups in an aqueous solution to form
------- & ---------.

hemiacetals and hemiketals.
HOW ARE THEY FORMED?

HOW IS A HEMIACETAL FORMED?

HOW IS A HEMIKETAL FORMED?

Two possible diastereomers that form because of cyclization are called --------.

two possible diastereomers that
form because of cyclization are called anomers.
HOW?

In the D-sugar form, when the anomer
hydroxyl is up it gives a -- ------- FORM.

In the D-sugar form, when the anomerhydroxyl is up it gives a -- ------- FORM.

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?

Haworth Structure of the B-D-Glucose....IS THE -OH ON THE FIRST CARBON DOWN OR UP?
MUST DRAW FOR TEST!!

Five-membered rings are called -------.

Six-membered rings are------

Cyclic form of fructose is ----------- ,
while glucose in the pyranose form
is --------------.

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?

This spontaneous process,--------- produces
an equilibrium mixture of a- and b-forms
in both furanose and pyranos ring
structures.

3 IMPORTANT MONOSACCHARIDES ARE NOTED IN LECTURE. GIVE THE HAWORTH FORM NAME OF THEM.

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?

HFCS—high fructose corn syrup—processed mixture of ------- & --------used as as a
sweetener. (combine to give ratios similar to table sugar—sucrose).

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
metabolism

-------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.

Reaction and Modification of Monosaccharides
NAME THE TOP 5

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
True False

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
certain enzymes.

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?
NAME 3

2 MAIN SUGARS IN HFCS
(high fructose corn syrup)

----- 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
---------.

---------- are produced by the reduction of aldehyde and ketone groups of monosaccharides

WHAT THE DIFFERENCE BETWEEN ALDITOLS AND ALDONIC ?

Sugar alcohols (alditols) are produced by the ------ of aldehyde and ketone groups of monosaccharides

EXAMPLE OF ALDITOL (SUGAR ALCOHOL) USED IN FOOD AND PHARMACEUTICALS.

REDUX OR OX?

D-glucose incubated in an alkaline (STRONG BASE) solution for several hours produces two isomers: D-mannose
and D-fructose...KNOWN AS WHAT?

DEFINE EPIMERIZATION

T OR F ?
The transformation of glucose to fructose is an aldose-ketose interconversion
True False

------Glycosidic linkages
form between oligosaccharides and the side chain amide nitrogen of certain
asparagine residues

------ Glycosidic linkages attach glycans to
the side chain hydroxyl of serine or threonine residues, or the hydroxyl oxygens of
membrane lipids

POST TRANSLATION MODIFICATIONS ARE A RESULT OF WHAT?

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?

WHAT 2 AMINO SUGARS ARE THE MOST COMMON AND OFTEN ATTACHED TO PROTEINS OR LIPIDS?

DEFINE Deoxy Sugars.

NAME 2 MONOSACCHARIDE DERIVATIVE GROUPS

In polysaccharides, large numbers of monosaccharides are linked together through ------ ----- OR ------ ------.

Naming of glycosides specifies the sugar component,
Acetals of glucose and fructose are ---- & ------.

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?

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 ------ & -------.

When the cyclic hemiacetal or hemiketal form
of the monosaccharide reacts with an alcohol, the new linkage is a--------- ---- AND THE COMPOUND IS A ----------.

2 monosaccharides
linked by a glycosidic bond IS CALLED WHAT?

GLYCOSIDIC BONDS CCAN OCCUR AT WHAT CARBON POSITIONS?

LABEL AND IDENTIFY THIS. MUST KNOW FOR TEST!

WHAT TYPE OF LINKAGE?

WHY IS LACTOSE A REDUCING SUGAR?

T OR F?
WHEN UTILIZING DISACCHARIDE NOMACLATURE, STRUCTURAL IDENTIFICATION AND BOND LINKAGE IDENTIFICATION ARE DONE TWO DIFFERENT/OPPOSITE WAYS.
True False

THE alpha(1,4) linkage between two molecules of glucose...DEFINE THE LINKAGE TYPE

-------- 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?

--------- 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!!!!

DEFINE THE ENTITE STRUCTURE AND THE 2 SUBUNITS. MUST KNOW FOR TEST!!

MUST KNOW THIS STRUCTURE:

One molecule of glucose linked to one molecule of fructose, linked by an a,b(1,2) glycosidic bond...WHAT AM I?

WHY IS LINKAGE NAMED DIFFERENTLY ON SUCROSE?

DEFINE UNIT, SUBUNITS AND NUMBER CARBONS.

Polysaccharides can be ---- OR ------.

Polysaccharides have been divided into two classes. NAME THEM

DEFINE HOMOGLYCAN POLYSACCHARIDES

WHAT 2 POLYSACCHARIDES WOULD YOU FIND IN FISH WRAPED IN PAPER?

energy reservoir of plant cells and a significant source of carbohydrate in the
human diet

Two polysaccharides occur together in starch. NAME THEM

----------- 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
150,000-600,000 D

----------- 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.

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?

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.

DEFINE Oligosaccharide