Behavioral Disorder: Schizophrenia & it's Case Study.pdf
Associate Professor of Pharmacognosy's Career Highlights
1. Associate Professor of Pharmacognosy , Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt
•Associate Professor, City of Scientific Research and Technological Applications (SRTA-City), Alexandria,
Egypt
•Senior research fellow, Liaoning University of Traditional Chinese Medicine, China (20118-2019)
•Visiting scholar, School of Pharmacy, University of Mississippi, USA (2012-2014)
Ahmed Metwaly
2. DEFINITION
I
(CH2O)n or H - C - OH
I
Carbo / hydrates
Polyhydroxy aldehydes or ketones, or substances that
upon hydrolysis yield polyhydroxy aldehydes or ketones.
3. - Desoxy sugars; rhamnose (C6H12O5),
cymarose (C7H14O4) and
digitoxose (C6H12O4),
- Sugar alcohols e.g. sorbitol (C6H14O6),
- Sugar acids e.g. gluconic acid (C6H12O7)
- Amino sugars e.g. glucosamine (C6H13NO5).
4. Photosynthesis
x CO2 + y H2O
Chlorophyll
Solar energy
Cx (H2O)y + x O2
Metabolism
C x (H2O) y + x O2 x CO
2 + y H2O + Energy
9. sugars are white, crystalline in shape and with sharp melting points, while
polysaccharides are white amorphous solids.
Sugars have a sweet taste (to various degrees) polysaccharides are tasteless.
monosaccharides are soluble in cold water and hot alcohol.
Polysaccharides are partially soluble in hot water and insoluble in alcohol
(cellulose is insoluble in all above mentioned solvents).
12. D & L designations are based
on the configuration about the
single asymmetric C in
glyceraldehyde.
The lower representations are
Fischer Projections. CHO
C
CH2OH
HO H
CHO
C
CH2OH
H OH
CHO
C
CH2OH
HO H
CHO
C
CH2OH
H OH
L-glyceraldehyde
D-glyceraldehyde
L-glyceraldehyde
D-glyceraldehyde
29. - AND - ANOMERS OF GLUCOSE:
➢When sugars undergo cyclization C-1 became a new chiral carbon and two
isomers exist.They are called “ Anomers”.
➢In the -anomer the OH group is directed downside and in the -anomer is
directed to the upper side.
➢These two forms have different specific rotation, in solution an equilibrium
exist between the two forms (mutarotation phenomenon).
O
H
HO
H
HO
H
OH
OH
H
H
OH
O
H
HO
H
HO
H
H
OH
H
OH
OH
O
H
OH
OH
H
H
OH
H
OH
CH2OH
H
O
H
OH
H
OH
H
OH
H
OH
CH2OH
H
Haworth formulations
Chair forms, pyranose structure
-D-glucopyranoside
-D-glucopyranoside -D-
glucopyranoside
-D-glucopyranoside
1
6
1
1
5 5
anomeric
proton
31. The evidence of cyclic configuration
▪ The existence of monosaccharides in ring rather than open chain structures and the size of the rings are
verified by X-ray analysis and is supported by:
1. The existence of two anomers for the same sugar, e.g. - and -glucose as proved by the formation of
two methyl glucosides.
2. The mutarotation phenomenon.
3. The difference in reactivity of glucose and other aldoses from true aldehydes (they do not give all the
characteristic reactions of aldehydes e.g. Schiff’s reaction).
- Aldoses and ketoses react with only one molecule of monohydric alcohol to give acetal unlike
normal aldehydes and ketones that react with two molecules (one molecule to give the hemiacetal and
another to transform the hemiacetal to acetal).
32. ▪Mutarotation: When a sugar is dissolved in water, the specific rotation of the
solution gradually changes until it reaches a constant value due to equilibrium between and
- forms ( form is more positive value)
▪ Mutarotation is the change in the optical rotation because of The change in the equilibrium
between two Anomers, when the corresponding Stereocenters interconvert.
e.g. Freshly prepared solution of -glucose has a specific rotation +18.7o. When this solution is
allowed to stand the rotation falls till reach + 52.7o.
33. Stereochemistry
C
C*
O
C*
C*
C*
CH2OH
H OH
HO H
H OH
H OH
H
C
C*
O
C*
C*
C*
CH2OH
HO H
H OH
HO H
HO H
H
D-glucose
L-glucose
Enantiomers Epimers
D-mannose D-galactose
Diastereomers
C
C*
O
C*
C*
C*
CH2OH
H OH
HO H
HO H
H OH
H
C
C*
O
C*
C*
C*
CH2OH
HO H
HO H
H OH
H OH
H
C
C*
O
C*
C*
C*
CH2OH
H OH
HO H
H OH
H OH
H
D-glucose D-mannose
C
C*
O
C*
C*
C*
CH2OH
HO H
HO H
H OH
H OH
H
Two sugars that differ in configuration at only one chiral center
Enantiomers
Diastereomers
Epimers
Mirror images
Pairs of isomers that have opposite configurations at one
or more chiral centers but are NOT mirror images
36. Aldoses (e.g., glucose) have an
aldehyde group at one end.
Ketoses (e.g., fructose) have
a keto group, usually at C2.
C
C OH
H
C H
HO
C OH
H
C OH
H
CH2OH
D-glucose
O
H
C H
HO
C OH
H
C OH
H
CH2OH
CH2OH
C O
D-fructose
37. Glucose and fructose have the same molecular formula C6H12O6. They
have different structures with different functional groups (different
connectivity). They are described as “structural isomers”.
CHO
CH
CH
CH
CH
CH2OH
OH
OH
HO
OH
CH2OH
C
CH
CH
CH
CH2OH
OH
OH
HO
D-Glucose D-Fructose
O
38. O H O H
C C
H – C – OH HO – C – H
HO – C – H H – C – OH
H – C – OH HO – C – H
H – C – OH HO – C – H
CH2OH CH2OH
D-glucose L-glucose
For sugars with more than
one chiral center, D or L
refers to the asymmetric C
farthest from the aldehyde or
keto group.
Most naturally occurring
sugars are d isomers.
39.
40. TERMS USED TO DESCRIBE ISOMERISM:
▪ Glucose and galactose are different from each other in the stereochemistry of carbon 4.
They are described as “4-epimers”.
▪ Glucose and mannose are different from each other in the stereochemistry of carbon 2.
They are described as “epimers”(also diastereoisomers)
CHO
CH
CH
CH
CH
CH2OH
OH
OH
HO
HO
D- Mannose
Epimers:
CHO
CH
CH
CH
CH
CH2OH
OH
OH
HO
OH
D-Glucose
CHO
CH
CH
CH
CH
CH2OH
OH
HO
OH
D-Galactose
HO
CHO
CH
CH
CH
CH
CH2OH
OH
OH
HO
OH
D-Glucose
43. An aldehyde can react with an
alcohol to form a hemiacetal.
A ketone can react with an alcohol
to form a hemiketal.
O C
H
R
OH
O C
R
R'
OH
C
R
R'
O
aldehyde alcohol hemiacetal
ketone alcohol hemiketal
C
H
R
O R'
R' OH
"R OH "R
+
+
44. Pentoses and hexoses can cyclize as
the ketone or aldehyde reacts with a
distal OH.
Glucose forms an intra-molecular
hemiacetal, as the C-1 aldehyde &
C-5 or react to form a 6-member
pyranose ring, named after pyran.
These representations of the cyclic sugars are called Haworth projections.
H O
OH
H
OH
H
OH
CH2OH
H
OH
H H O
OH
H
OH
H
OH
CH2OH
H
H
OH
-D-glucose -D-glucose
2
3
4
5
6
1 1
6
5
4
3 2
H
CHO
C OH
C H
HO
C OH
H
C OH
H
CH2OH
1
5
2
3
4
6
D-glucose
(linear form)
45. ▪ Any carbohydrate + Alcoholic -naphthol then add conc. H2SO4 on the wall of the
test tube Violet ring between the two layers.
Treatment with conc. mineral acid (HCl or H2SO4) leads to
dehydration of sugars and formation of the corresponding
furfural.
O CHO
O CHO
HOH2C
Pentoses
Hexoses
Furfural
(volatile)
5-Hydroxymethyl
furfural
(less volatile)
Dehydration
Dehydration
46.
47. ▪ Reaction of furfural with amines resulted in Schiff’s bases with different colors used as
color tests.
▪ (Differentiate between Pentoses and Hexoses):
▪ Pentose + conc. acid and heat, expose the vapours to Aniline acetate paper Red colour
▪ Hexoses give negative result.
(for keto-hexoses):
Sugar solution + few crystals of Resorcinol + Equal volume of
conc. HCl and warm on water bath Rose Red Colour.
48. ▪ Sugar (H2O)+ phenyl hydrazine hcl+ naac, heat (50 min), cool examine ozazone crystals
under the microscope. The ozazone are yellow, crystalline with sharp m.P. Glucose,
mannose fructose will give the same crystals (reaction involves C-1 and C-2) due to
destruction of asymmetric center at C-2.
CHO
CHOH
3 PhNH-NH2
CH=N-NH-Ph
CH=N-NH-Ph
Ozazone crystals
+ Ph-NH2 + NH3
(characteristic)
sugar
phenyl hydrazine HCl
49. O
HO
OH OH
CH2OH
HO
C6H5NHNH2
via open-chain form D-glucose
C OH
H
HO
OH
H
OH
H
CH2OH
CH
OH
H
H
HO
OH
H
OH
H
CH2OH
CH
C
H
HO
OH
H
OH
H
CH2OH
NNHC6H5
CHNHNHC6H5
C O
H
HO
OH
H
OH
H
CH2OH
CH2NHNHC6H5
C6H5NHNH2
C NNHC6H5
H
HO
OH
H
OH
H
CH2OH
CH2NHNHC6H5
C N
H
HO
OH
H
OH
H
CH2OH
CH NH NHC6H5
NHC6H5
H
NH
NNHC6H5
C6H5NHNH2
-NH3
-C6H5NH2
CH
C
H
HO
OH
H
OH
H
CH2OH
NNHC6H5
NNHC6H5
D-Mannose phenylosazone
or D-glucoe phenylosazone
50. CH
C
H
HO
OH
H
OH
H
CH2OH
NNHC6H5
NNHC6H5
D-Mannose phenylosazone
or D-glucoe phenylosazone
N N
H
N
R
NHC6H5
C6H5
Where R =
HO H
H OH
CH2OH
H OH
· Notice that the asymmetry at C-2 is lost, so that D-glucose, D-mannose, and D-fructose
all form the same osazone.
·The reaction does not continue further down the chain to C-3 by a similar series of steps
possibly because of stabilization of the osazone due to hydrogen-bonding
51.
52. n
COOH
CH2OH
(H OH)
CHO
CH2OH
(H OH)n Mild Oxidation
Br2
CHO
CH2OH
(H OH)n
HNO3
Strong Oxidation n
COOH
COOH
(H OH)
Glucaric acid
(Acyclic St.)
Protection
Oxidation
CHO
CH2OH
(H OH)n
Glucuronic acid
(cyclic St.)
n
CHO
COOH
(H OH)
Gluconic acid
(Acyclic St.)
53. ▪ These are oxidizing agents like Bromine water (or I2) that
convert the CHO group to COOH to produce “onic acids”.
▪ N.B. Ca gluconate (I.V. or orally) is used in case of calcium therapy,
Ferrous gluconate (I.V. or orally) is used in iron deficiency.
CHO
CH
CH
CH
CH
CH2OH
OH
OH
HO
OH
D-Glucose
COOH
CH
CH
CH
CH
CH2OH
OH
OH
HO
OH
Gluconic acid
I2 or Fehling's
54. ▪ These are oxidizing agents like HNO3 that convert the CHO and CH2OH group to COOH to
produce “aric acids”.
CHO
CH
CH
CH
CH
CH2OH
OH
OH
HO
OH
D-Glucose
COOH
CH
CH
CH
CH
COOH
OH
OH
HO
OH
Saccharic acid
HNO3
55. ▪Glalactaric acid (Mucic acid) test:
▪Oxidation of galactose resulted in the formation of
Galactaric acid. It is a meso compound insoluble in
water and have zero optical rotation.
CHO
CH
CH
CH
CH
CH2OH
OH
HO
OH
D-Galactose
COOH
CH
CH
CH
CH
COOH
OH
HO
OH
Galactaric acid
HNO3
HO HO
56. ▪ It is carried out by first protecting the – CHO group, followed by oxidation of the -
CH2OH group, or in one step by using enzyme to give aldouronic acid, e.g. oxidation of
glucose into glucuronic acid.
CHO
CH
CH
CH
CH
CH2OH
OH
OH
HO
OH
D-Glucose
CHO
CH
CH
CH
CH
COOH
OH
OH
HO
OH
Glucuronic acid
O
COOH
H
H
OHOH
H
H
OH
OH
H
57. ▪ This resulted in the reduction of the CHO to CH2OH producing “sugar alcohols”. Sodium borohydride or
H2/pt are examples of reducing agents.
▪ E.G. Glucose reduced to sorbitol which act as mild laxative while mannose reduced to mannitol which is
used as osmotic diuretic, vasodilator and in lab. Diagnosis of kidney function.
CHO
CH
CH
CH
CH
CH2OH
OH
OH
HO
OH
D-Glucose
CH2OH
CH
CH
CH
CH
CH2OH
OH
OH
HO
OH
Sorbitol
H2/Pt
58. 58
CH O
HO H
HO H
H OH
H OH
CH2OH
D-mannose
CH2OH
HO H
HO H
H OH
H OH
CH2OH
NaBH4
H2O
D-mannitol
"does not promote tooth decay"
"not non-caloric"