CARBS (MAIN)

100+/120 cutie!!!!!!

Glucose

Most important carbohydrate in the body is

(CnH2O)n or “hydrate of carbon”

The empiric for many of the simpler carbohydrates is

Glycosidic bond

Type of bonding of carbohydrates

3. Hormones

Carbohydrates are components of the following except?
1. Cell membranes
2. Nucleic acids
3. Hormones
4. Bacterial cell wall

carbohydrates

Serve as intermediates for the biosynthesis of
biochemical entities such as lipids, proteins, and nucleic acid

1 and 2

Which of the following is an example of monosaccharide?
1. Ribose 2. Galactose 3. Amylose 4. Lactose

Lactose and Cellobiose

Which has/have β (1,4) linkages
1. Lactose 2. Maltose 3. Cellobiose 4. Sucrose

Carbohydrate

Part of the structural framework of DNA and RNA molecules

T

T OR F?
Every carbon (C) contains your hydroxyl group
(OH) except the carbon that is double bonded
with your oxygen.

Polysaccharides

has more than 10 sugar units

Oligosaccharides

3-10 sugar units

Disaccharide

Maltose
Sucrose
Lactose

Glyceraldehyde ; Dehydroxyacetone

Trioses

Aldose _________ ; Ketose ___________

Erythrose, Threose ; Erythlurose

Tetroses

Aldose _________ ; Ketose ___________

Xylose, Ribose, Arabinose ; Ribulose

Pentoses

Aldose _________ ; Ketose ___________

Glucose Galactose Mannose ; Fructose

Hexoses

Aldose _________ ; Ketose ___________

Glucose

a known aldose

Fructose

a known ketose

Isomers

are molecules that have the same chemical
formula but different structures

Stereoisomers

differ in the 3-D orientation of atoms

optical isomers

Most biologically important chemicals exist as
stereoisomers or also called

D/L Isomerism

are also called enantiomers or mirror images of
each other.

ASYMMETRIC OR CHIRAL CARBON

Carbon attached to four
different groups

ANOMERIC CARBON

Carbon in the carbonyl
group

PENULTIMATE CARBON

The highest numbered chiral carbon or the last chiral carbon

Bel-van't Hoff rule

states that the number of stereoisomers of an organic compound is 2
n, where n is the number of chiral carbon atoms.

D-TALOSE

D-Gulose

D-Galactose

D-ALLOSE

Name in order

EPIMERS

Stereoisomers with more than one chiral carbon which differ in chirality at ONLY ONE chiral center.

EPIMERASE; EPIMERIZATION

Interconversion of epimers catalyzed by
enzyme ___________ and the process is called ________

Solid
Soluble
Solubility

_________at room temperature
_________in water
_________helps carbs to be transported
quickly

same

Molecules which are enantiomers of each other have _______ (same or diff) physical properties (melting point, boiling point, index of refraction, etc.)

Polarized

vibrates only in one plane; it results from passing light through a polarizing filter.

Dextrorotatory (+)(d)(r)

- Rotate the light to the right or clockwise

Levorotatory (-)(l)(s)

- Rotate the light to the left or counterclockwise

A racemic mixture, or racemate

is a solution in which both enantiomers of a substance are present in equal proportions

Light Source, Unpolarized light, Polarizer, Tube with chemicals, Analyzer, Polarized Light, Observer

Process of Optical Activity

FISCHER PROJECTION

Specific type of formula that designates the
orientation of groups

two crossed lines

To construct a 3D based on Fischer projections, atetrahedral carbon atom is represented by

RING CONFIGURATION

is formed as a self-reaction when the carbonyl atom forms a hemiacetal linkage for aldoses and hemiketal linkage for ketoses

pYRANOSE

a six-membered ring

FURANOSE

A five-membered ring

ANOMERS

Are formed when sugars assume a cyclic form. This is an isometric form of monosaccharides that differ only in their configuration about the hemiacetal or hemiketal carbon atom.

TRUE

TRUE OR FALSE
The carbon atom where a carbonyl or functional group is present is now called the anomeric carbon.

Mutarotation

epimers: epimerization; anomers __________

- When the alpha or beta anomers are interconverted

define whether alpha or beta

Right side

If the cyclic structure is alpha, on what side is the OH located in its Fischer projection?

BETA

Define whether the structure is beta or alpha when it cyclicize

. HAWORTH PROJECTION

is considered as more realistic than fischer projection

Haworth Projection

Biochemists prefer what type of projection?

NEWMANN OR CHAIR

Organic Chemists prefers which type of structure?

__________ is the carbon immediately to the right of the oxygen atom

Last carbon is drawn below/above the plane

below: L-Sugar mnemonic (L-ow)
above: D-sugar

How do we determine if the Haworth projection is D or L?

a-l-glucopyranose

Determine if alpha/beta and D/L

NEWMAN/CONFORMATIONALCHAIR FORM

The configuration that best represents the
three-dimensional conformation of sugars with 5 or more carbons

D-Glucose

can be obtained from fruit juices, hydrolysis of starch, cane sugar, maltose and lactose

D-fructose

From fruit juice, honey, can sugar, and INULIN

D-GALACTOSE

From hydrolysis of lactose

D-RIbose

-sourced from Nucleic Acid
- structural components of nucleic acid and coenzymes and flavoprotein
- an intermediate in the PPP

D-Galactose

can be changed in the liver and be metabolized and synthesized in the mammary gland to make lactose of milk

components of glycolipids and glycoprotein

D-Galactose

associated with cataract and galactosemia

D-Fructose

can be changed into glucose int he liver

PENTOSE PHOSPHATE PATHWAY

is able of converting something into energy like glucose

F

T OR F All reducing sugars are monosaccharides

D-Mannose

Constituent of glycoprotein and sourced from hydrolysis of plant mannan gums

carbohydrates are completely oxidized
to carbon dioxide and water molecules

In carbs as reducing agents, the highest energy yield from carbohydrates occurs
when...

true

*Reverse complete oxidation of sugars is the
reduction of CO2 and water molecules to
produce sugar which happens in the process of
photosynthesis. T OR F?

ferric (Fe3+) or cupric (Cu2+).

Monosaccharides can be oxidized by relatively mild oxidizing agents such as...

reducing sugars.

Sugars capable of reducing ferric or cupric ion are

OXIDATION

What type of reaction is involved when a carbonyl group forms carboxylic acid

First one is an aldose/aldehyde (the carbonyl group) being converted to carboxyl

Second one (R-CH2OH to R-COOH) is the terminal carbon

Note: Ketoses are resistant to oxidation since they do not have Hydrogen in their carbonyl group (oxidation removes hydrogen)

R-CHO -> R-COOH
R-CH2OH -> R-COOH

explain

TRUE

Acidic sugar contains a carboxylate group which confers that negative charge at neutral pH is true for that monosaccharide

true

When these aldehydes are oxidized, the oxidizing agent must be reduced and that is the time when we detect if the sugar is non-reducing.

true or false

Uronic Acid
Aldonic Acid
Aldaric

Three products/examples of oxidation

Uronic Acid

when an aldehyde group is left intact and primary alcohol at the other end is oxidized to COOH

Aldonic Acid

when the aldehyde group is converted to carboxyl group

Aldaric Acid

when both ends of a monosaccharide
is oxidized

Gluconic Acid

Identify what type of oxidation product and what name

glucuronic acid

glucuronic acid Identify what type of oxidation product and what name

Identify what type of oxidation product and what name

.

NAME THE FF

REDUCTION OF CARBONYL

- It is the gain of electrons
- The resultant product is a polyol or sugar alcohol
(alditol)

Sugar Alcohol

erythritol, lactitol, maltitol, mannitol, sorbitol, and xylitol are examples of

Glucose from sorbitol

- Most important sugar alcohol
- Associated with cataracts with diabetes

Mannose from mannitol

- Important as diuretic
- Glyceraldehyde gives glycerol

Formation of Glucitol though Reduction of Carbonyl Group

Wat reaction and product is formed here

Esters through ESTERIFICATION

__________ are formed by reaction of hydroxyl groups (alcohols) with acids.

ESTERIFICATION OF THE HYDROXYL GROUP (in CH2OH) OF CARBOHYDRATE

Explain the reaction below

AMINO DERIVATIVES

- Sugar + Amin group (NH2
- Monosaccharides in which the alcoholic hydroxyl group is replaced by an amino acid

Amino dERIVATIVE

FERMENTATION

- Used for food industry
- For bacterial identification
- GLUCOSE contributes to this reaction by converting ADP to ATP

OSAZONE FORMATION

- It is seldom used for identification as we now use HPLC or mass spectrometry
- It consists of monosaccharide with phenylhydrazone to form a crystalline compound D-fructose and D-mannose

dehydration synthesis

Disaccharides are formed by joining two simple sugars through__________ forming a covalent bond between them

DISACCHARIDE

The hydroxyl group of one monosaccharide
combines with the hydrogen of another
forming a glycosidic linkage

TRUE

Even though disaccharides are soluble in water, they are too large to pass through the cell membrane

DISACCHARIDES

Sucrose, Maltose, Lactose, Cellobiose are examples of

Lactose
Sucrose
Maltose
Cellobiose

NAME THE DISACCHARIDES

Linkage between galactose and glucose ______
Linkage between Fructose and Glucose_____
Linkage between two glucose (beta) ______
Linkage between two glucose (alpha) ________