CHAPTER 4: GLUCIDE

4.1. Function of glucide

4.2. Classification of glucide

4.3. Monosaccharides

4.4. Oligosaccharides

4.4. Polysaccharides

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4.1. Function of glucide

- The oxidation of carbohydrates is the central energy-yielding pathway

- Reserve substances. Ex: starch, glycogen

- Structural substances. Ex: cellulose, chitin

- Protective elements. Ex: glycosaminoglycans are found in connective

tissue and soft tissue in humans and animals.

- Components of many bioactive compounds: enzymes, hormones.

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4.1. Function of glucide

Proteoglycans make up a major part of the extracellular

matrix, filling the spaces that occur between cells.

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4.2. Classification of glucide

- Simple glucide: monosaccharide

- Complex glucide

+ Oligosaccharide: contain 2-10 monosaccharides joined by glycosidic

bonds

+ Polysaccharide (glycans) : contain many monosaccharides joined by

glycosidic bonds

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4.3. Monosaccharides

4.3.1. Structure of monosaccharides

- Monosaccharides are aldehyde derivatives or ketone derivatives of
polyols.

- Aldoses: CH2 OH CHO

-2H
CHOH CHOH
CH2 OH CH2 OH
Glycerin Glyceraldehyde

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4.3. Monosaccharides

4.3.1. Structure of monosaccharides

- Ketoses
CH 2 OH CH 2 OH
-2H
CHOH CO

CH2 OH CH 2 OH
Glycerin dihydroxyacetone

- Monosaccharides with three, four, five, six carbon atoms in their

backbones are called, respectively, triose, tetroses, pentoses, hexoses.

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4.3.1. Structure of monosaccharides

 Linear Structures (Dạng cấu trúc mạch thẳng): Fischer projections

- L and D isomeric forms

- Most of the hexoses of living organisms are D isomers
1 CHO 1 CHO
H 2 C OH H 2 C OH
HO 3
C H HO 3
C H
H 4
C OH H 4
C OH
H C
5
OH HO 5
C H
CH 2 OH
6 CH 2 OH
6
D(+) Glucose L(-) Glucose
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4.3.1. Structure of monosaccharides
 Cyclic Structures:
- These five-membered ring compounds are called furanose
- These six-membered ring compounds are called pyranose

OH H
H OH
1C
1 C
H C
2 OH
H 2 C OH
HO C
3
H O
HO C
3
H O
H 4C OH
H C
4 OH
H 5
C
H 5
C CH 2OH
6

6 CH 2 OH  – D - glucose
 – D - glucose

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4.3.1. Structure of monosaccharides
 Cyclic Structures:
Haworth perspective formulas
Aldose:
- Furanose: formed between – CHO and – OH of C4
- Pyranose: formed between – CHO and – OH of C5
Ketose
- Furanose: formed between – CO and – OH of C5
- Pyranose: formed between – CO and – OH of C6

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4.3.1. Structure of
monosaccharides
 Cyclic Structures:

Formation of the two cyclic

forms of D-glucose. Reaction
between the aldehyde group at
C-1 and the hydroxyl group at C-
5 forms a hemiacetal linkage,
producing either of two
stereoisomers, the α and β
anomers, which differ only in the
stereochemistry around the
hemiacetal carbon.

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4.3.1. Structure of monosaccharides
 Cyclic Structures:

The pyranose forms of D glucose

and the furanose forms of D-
fructose are shown here as Haworth
perspective formulas. The edges of
the ring nearest the reader are
represented by bold lines. Hydroxyl
groups below the plane of the ring
in these Haworth perspectives
would appear at the right side of a
Fischer projection. Pyran and furan
are shown for comparison.

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4.3.2. Important monosaccharides:
4.3.2.1. Pentose: 1 CHO
 L – arabinose: H 2 C OH
- Component of biopolymers such
HO C H
as hemicellulose, pentosan 3

- Its absorption by human body or yeast is HO C H

4
poor.
CH2OH
5
- L-arabinose is in fact more common than D-
arabinose in nature L - arabinose

5 4
CH2OH
1
OH 4
1 2
OH 3
2 3
OH

α-L-arabinofuranose
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4.3.2. Important monosaccharides:
4.3.2.1. Pentose:
 L – arabinose:

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4.3.2.1. Pentose:

 D – xylose: 1 CHO
- Component of biopolymers such as H C OH
2

xylan và pentosan in wood and thatch C

HO 3
H
- Not absorbed by yeast or human body
H 4
C OH
- Used for xylitol production CH OH
5 2

– xylose
DD -xilose

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4.3.2.1. Pentose:

 D – xylose:

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4.3.2.1. Pentose:

 D –ribose:

- Component of ribonucleic acid, vitamin B2 (riboflavin) and nicotine

amide dinucleotide coenzyme.

- D – deoxyribose is a component of DNA

- D-ribose-5-phosphate is available for the manufacturing of the amino

acids tryptophan and histidine, or for use in the pentose phosphate
pathway.

- The absorption of D-ribose is 88–100% in the small intestines.

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4.3.2.1. Pentose:

 D –ribose:

1CHO

H 2C OH
H 3C OH
H 4C OH

5
CH2OH
D -ribose

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4.3.2.2. Hexose:
 D - Glucose:

- aldose, hexose, pyranose.

- also called dextrose, found in grapes 1 CHO

- a component of starch, cellulose and glycogen H 2C OH

- absorbed essily by yeast or human body HO 3C H
- used for glucitol (sorbitol) production H 4 C OH
H C
5
OH
CH 2 OH
6
D(+) Glucose
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4.3.2.2. Hexose:
 D - Glucose:

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4.3.2.2. Hexose:

 D – mannose:

- aldose, hexose, pyranose.

- Is a component of hemicellulose

- Absorbed essily by yeast or human body

D – mannose

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4.3.2.2. Hexose:

 D – galactose:

- aldose, hexose, pyranose.

- It is found in galactan, lactose and agar

- D-Galacturonic acid is the main component

of pectin
- Absorbed by a few yeasts
D – galactose

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4.3.2.2. Hexose:
 D – fructose:
- hexose, ketose, furanose

- also called levulose

- Fructose is found in honey, fruits

- Pure, dry fructose is a very sweet, white, odorless,

crystalline solid and is the most water-soluble of
all the sugars

- Absorbed essily by yeast or human body

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4.3.2.2. Hexose:
 D – fructose:

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4.3.3 Characters of monosaccharide

4.3.3.1 Monosaccharides Are Reducing Sugars

- Monosaccharides can be oxidized by oxidizing agents

- Product depends on type of oxidizing agent (mild or strong)

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4.3.3.1 Reducing character:
 Mild oxidizing agent:
- Monosaccharides can be oxidized mild oxidizing agents such as Br2,
I2, Cl2 or Cu2+ and Fe3+
- only aldehydic group is oxidized to –COOH group
1CHO 1 COOH

H 2C OH H 2 C OH
HO C H HO C H
3 Br 2 3

H 4
C OH H C OH + 2HBr
OH- 4

H 5
C OH H C
5
OH

6
CH2OH CH2 OH
6

Glucose Acid gluconic

(acid aldonic)
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4.3.3.1 Reducing character:

 Mild oxidizing agent:

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 CHAPTER 4: GLUCIDE

4.3.3.1 Reducing
character:
 Mild oxidizing
agent:
- This property is the
basis of Fehling’s
reaction, a qualitative
test for the presence
of reducing sugar.

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4.3.3.1 Reducing character:
 Strong oxidizing agent:
- A strong oxidizing agent such as HNO3 can oxidize the aldehyde and
the alcohol groups
1 CHO 1 COOH
H 2 C OH H 2 C OH
HO 3
C H HO 3
C H
HNO 3
H 4
C OH + [O] H 4
C OH
Strong oxidation
H 5
C OH H 5
C OH
6 CH 2 OH 6 COOH
Glucose Acid glucaric
(acic aldaric)

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4.3.3.1 Reducing character:
 OH glucoside is protected before the oxidation:
- First, methylate or acetylate OH - glucoside group
- only primary alcohol group is oxidized to carboxyl group

CH2OH CH2OH COOH

H H O OH glucoside O O H
H is protected H H H Br 2 H H
OH H OH H OH H
HO OH HO OR HO OR
H OH H OH H OH
Glucose Acid glucuronic

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 CHAPTER 4: GLUCIDE

4.3.3.1 Reducing character:

 OH glucoside is protected before the oxidation:

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4.3.3.2 Oxidizing character:
- Monosaccharides can be reduced by reducing agent
- The carbonyl group is turned into an alcohol group.
- The products named by replacing the ose ending with -itol.

1 CHO 1 CH2 OH
H 2 C OH H 2 C OH
HO 3
C H HO 3
C H
Hg + Na
H 4
C OH + 2H H 4
C OH
H 5
C OH H 5
C OH

6 CH2 OH CH2OH
6

Glucose Sorbitol

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4.3.3.3 Glycoside formation

- Characteristic reaction for OH hemiacetal

- Glycoside in natural: anthocyanins provide the red, purple and blue

colors; nicotine; saponin..

- When the alcohol component of a glycoside is provided by a hydroxyl

function on another monosaccharide, the compound is called
a disaccharide

- Derivatives formed when a monosaccharide reacts with an non-sugar

called glycoside

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4.3.3.3 Glycoside formation

Nicotine N-D-Glucoside

Saponin
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4.3.3.4 Esterification

- free OH groups of carbohydrates can be converted to esters by

reactions with acids

- the phosphorylation of alcohol groups in glucose is a critical

metabolic step.

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4.3.3.4 Maillard reaction

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4.3.3.4 Maillard reaction

- Maillard reactions refer to a chemical reaction between an amino

acid and a reducing sugar such as glucose and fructose in the presence
of heat

- The reaction temperature: 35 C - 100 C, >100 C

- create a wide range of flavor, odor, and/or noticeable browning color

compounds called melanoidin.

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4.3.3.4 Maillard reaction

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4.4. Oligosaccharide

- Oligosaccharides are short polymers of several monosaccharides (2-

10) joined by glycosidic bonds.

- Powdery or crystalline, soluble in water and sweet in taste.

- can be hydrolysed by enzymes or acids to yield monosaccharides.

- The common and important oligosaccharides are disaccharide.

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4.4. Oligosaccharide

4.4.1 Disaccharide:

Disaccharides consist of two monosaccharides joined covalently

by an glycosidic bond. There are two forms:

+ Reducing disaccharide: has free hemiacetal OH group

+ Non reducing disaccharide: has no free hemiacetal OH group.

Sucrose

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4.4.1 Disaccharide:
 Maltose:
- maltose contains two α-D-glucose residues joined by a glycosidic
linkage between C-1 (the anomeric carbon) of one glucose residue
and C-4 of the other
- maltose is a reducing sugar
- called malt sugar
- can be hydrolysed by maltase or acids

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4.4.1 Disaccharide:
 Saccharose (sucrose):
- Saccharose contains α-D-glucose and β-D-fructose residues joined
by a α – 1,2 – glycosidic linkage  Sucrose is a nonreducing
sugar.
- Found in cane and sugar beet

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4.4.1 Disaccharide:
 Saccharose (sucrose):
Caramelization: is a distinct non-enzymatic browning process.
However, unlike Maillard reactions which require the availability of
sugars and free amino groups, caramelization takes place using only
sugars as substrates.

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4.4.1 Disaccharide:
 Saccharose (sucrose):
Sugar inversion
Invertase or acid can be used for the hydrolysis of sucrose into glucose
and fructose. The resulting invert sugar syrup is sweeter than sucrose.

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4.4.1 Disaccharide:
 Lactose:
- Contains β – D galactose and α or β– D – glucose residues joined by a
β – 1,4 – glycosidic linkage  lactose is a reducing sugar
- occurs naturally only in human and animal’s milk (5 to 8% lactose by
weight)
- can be hydrolysed by acids or β – galactosidase

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4.4.1 Disaccharide:

 Cellobiose

- contains two β-D-glucose residues joined by a β – 1,4 – glycosidic

linkage

- is the component of cellulose

- can be hydrolysed by acids or cellobiase

- is a reducing sugar

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4.4.1 Disaccharide:

 Trehalose

- contains two α-D-glucose residues joined by a α – 1,1 – glycosidic

linkage

- Found in mushroom, also called mushroom sugar

- can be hydrolysed by acids or trehalase

- is a nonreducing sugar

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4.4.2 Trisaccharide:
- Raffinose is a trisaccharide composed of α-D-galactose, α-D-glucose,
and β-D-fructose
- It can be found in sugar beet and molasses

Melibiose

- D - Galactose - D - Glucose  - D - Fructose

CH2 OH CH2
O O
HO H H O H H H CH2OH H
O
OH H OH H O H OH
H OH CH2 OH
H OH H OH OH H
Rafinose

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4.4.3. Relative sweetness:

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4.4. Polysaccharides:

- Polysaccharides consist of many monosaccharides joined covalently

by glycosidic bonds

- Two types of polysacccharides:

+ Homopolysaccharides

+ Heteropolysaccharides

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4.4. Polysaccharides

- The classification of carbohydrates is based on their source

+ Plant Polysaccharides

+ Microorganism Polysaccharides

+ Animal Polysaccharides

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4.4.1. Plant polysaccharides

4.4.1.1 Starch:

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4.4.1. Plant polysaccharides

4.4.1.1 Starch:

 Structure:

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4.4.1.1 Starch:
Amylose Amylopectin

Formed by alpha D-glucose

- Contains α-1,4-glycosidic bonds - Contains α-1,4-glycosidic and α-1,6-

 amylose has a linear structure glycosidic bond  amylopectin has a
branched structure
- Dissolved in warm water. - Dissolved in hot water.
- Amylose solution has low viscosity - Amylopectin solution has high
viscosity
- Iodine molecule will bind with the - Iodine molecule will bind with the
helical chain of amylose, hence give helical chain of amylopectin, hence
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the blue color give the purple color
 CHAPTER 4: GLUCIDE

4.4.1.1 Starch:

 Gelatinization and liquefaction of starch:

- Gelatinization of starch: is the process where starch and water are

subjected to heat, causing the starch granules to swell. This gives the
starch solution a viscous

- Liquefaction of starch: is the process involving the partial hydrolysis

of the starch, with concomitant loss in viscosity.

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4.4.1.1 Starch:

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4.4.1.1 Starch:

 Enzymes in starch hydrolysis:

- Alpha – amylase: liquefaction enzyme

- Beta – amylase: saccharification enzyme

- Gamma – amylase: saccharification enzyme

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4.4.1.1 Starch:

 Enzymes in starch hydrolysis:

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4.4.1.2. Inulin

- Consist of fructoses linked of β - 2,1 –

glycosidic and a chain-terminating glucose

- Plants that contain high concentrations of

inulin include: peony root (rễ mẫu đơn),
white mustard (cây cải trắng), Grasses (cây
hòa thảo)

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4.4.1.3. Cellulose

- It is formed by cellobiose (or β – D – glucose) units, linked by beta-

1,4 -glycosidic linkages
CH 2 OH CH 2 OH CH 2 OH CH 2 OH
O O O O
H H H H H H H H
OH H O O O
OH H OH H OH H
H H H H
H OH H OH H OH H OH
Cellulose

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4.4.1.3. Cellulose

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4.4.1.3. Cellulose

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4.4.1.3. Cellulose

- Enzymatic hydrolysis of cellulose

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4.4.1.4. Hemicellulose

- Hemicelluloses are polysaccharides in plant cell walls

- Hemicelluloses include xyloglucans, xylans, mannans and

glucomannans, and beta-(1-->3,1-->4)-glucans

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4.4.1.5. Pectin

- Pectin, a polysaccharide, is composed primarily of essentially linear

polymers of D-galacturonic acid units joined in α- (1→4) glycosidic
linkages; the polymer chains are esterified to various degrees with
methanol

COOCH3 COOH COOCH3

O O O
H H H H H H
O O
OH H OH H OH H
H H H

H OH H OH H OH

- Protopectin and Pectin

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4.4.1.5. Pectin

In the early stage of development of fruits, the pectic substance is a water-

insoluble protopectin which is converted into pectin by the enzyme
protopectinase during ripening of fruit.
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4.4.1.5. Pectin

- Hydrolysis of pectin: pectic substances cause haziness and high

viscosity of fruit juices. Pectinase enzymes are biological compounds
that degrade pectic compounds.

+ CH3OH

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4.4.1.5. Pectin

- Gel forming:

+ High methoxyl-pectins (> 50% esterified, usually ≈ 67%) gel by the

formation of hydrogen-bonding and hydrophobic interactions in the
presence of acids (pH ≈ 3.0 – 3.5) and sugars (for example, about ≈ 65%
sucrose)
+ Low methoxyl pectins (< 50%
esterified) form gels in the
presence of calcium ions and at
low pH (3 - 4.5)
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4.4.1.6. Agar: agar occurs as structural carbohydrate in the cell walls of

agarophytes algae

 Agarose: consisting of chains of repeating alternate units of β-1,3-

linked- D-galactose and α-1,4-linked 3,6-anhydro-L-galactose

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4.4.1.6. Agar

 Agaropectin: is a sulfated polysaccharide (3% to 10% sulfate) from

agarose

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4.4.2. Microorganism polysaccharide

- Dextrans are bacterial and yeast polysaccharides made up of α-1,6 -

linked poly-D-glucose; all have α-1,3 branches, and some also have α-
1,2 or α-1,4 branches.

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4.4.3. Animal polysaccharide

4.4.3.1. Glycogen:

- The structure of glycogen is similar to amylopectin but more branched.

Glycogen: α-1,4/ α-1,6 ~ 12/1; Amylopectin: α-1,4/ α-1,6 ~ 25/1

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4.4.3. Animal polysaccharide
4.4.3.2. Chitin:
- Chitin is the principal component of the hard exoskeletons of nearly a
million species of arthropods
- Chitin is a linear polysaccharide composed of N-acetylglucosamine
residues in β-1,4 linkage. The only chemical difference from cellulose
is the replacement of the hydroxyl group at C-2 with an acetylated
amino group.

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4.4.3. Animal polysaccharide
4.4.3.2. Chitin:

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