- Carbohydrates are composed of carbon, hydrogen, and oxygen. They include sugars, starches, and cellulose. - Monosaccharides are the simplest form of carbohydrates and include glucose, fructose, and galactose. Disaccharides are formed from two monosaccharides and include sucrose and lactose. - Carbohydrates can exist as linear or cyclic structures. Cyclic forms include glucose existing as glucopyranose or glucfuranose. - Structural isomers of carbohydrates differ in bonding configuration but have the same molecular formula. Examples include glucose and fructose.

1. ,D ZKKY
D
h ' '

2. •
,
K

3. 'EZ , Z dZ/^d/^
• The term carbohydrate is derived from the french:
hydrate de carbone
• Compounds composed of C, H, and O
• (CH2O)n when n = 5 then C5H10O5
• Not all carbohydrates have this empirical formula:
deoxysugars, aminosugars etc,,
• Carbohydrates are the most abundant compounds
found in nature (cellulose: 100 billion tons
annually)

4. '
• D
•W
•'
• '
• '
• D
• E

5. • ^
• /
•
•
• W

6. I
(CH2O)n or H - C - OH
I
d
, K

7. D K,
K
• W
W
•,
•,
•

8. D
•
•
d
t
• D
•
•

9. D
d
• D
•

10. D
H O
C CH2OH
H C OH C O
HO C H HO C H
H C OH H C OH
H C OH H C OH
CH2OH CH2OH
D-glucose D-fructose

11. CH 2OH CH 2OH
CH 2OH
CH 2OH
C O C O CH 2OH
C O
C O
(H C OH)n H C OH C O
H C OH
CH 2OH
CH 2OH H C OH H C OH
CH 2OH
CH 2OH H OH
Ketose Ketotriose Ketotetrose
n=1 Ketopentose H C OH
n=0
n=2
CH 2OH
Ketohexose
n=3

12. H H H H H
C O C O C O C O C O
(H C OH)n H C OH H C OH H C OH H C OH
CH2OH CH2OH H C OH H C OH H C OH
Aldose Aldotriose CH2OH H C OH H C OH
n=1
Aldotetrose CH2OH
n=2 H C OH
Aldopentose
CH2OH
n=3
Aldohexose
n=4

13. CHO CHO
H C OH HO C H
CH2OH CH2OH
D-glyceraldehyde L-glyceraldehyde
CHO CHO
H C OH HO C H
CH2OH CH2OH
D-glyceraldehyde L-glyceraldehyde

14. ^

15. ^ E
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
D-glucose L-glucose

16. O H O H
C C
d H – C – OH HO – C – H
HO – C – H H – C – OH
H – C – OH HO – C – H
K H – C – OH HO – C – H
CH2OH CH2OH
D-glucose L-glucose
d
d d

17. ,
H H
C O + R' OH R' O C OH
R R
aldehyde alcohol hemiacetal
R R
C O + R OH R O C OH
R' R'
ketone alcohol hemiketal

18. CHO
W 1
H C OH
2
HO C H D-glucose
3
H C OH (linear form)
K, 4
H C OH
' 5
CH2OH
6
6 CH2OH 6 CH2OH
5 O 5 O
H H H OH
K, H H
4 H 1 4 H 1
OH OH
OH OH OH H
3 2 3 2
H OH H OH
α-D-glucose β-D-glucose
d
,

19. 1
CH2OH
2C O
HO C H
1 CH2OH
3 HOH2C 6 O
H C OH
4 5 H HO 2
H C OH H 4 3 OH
5
OH H
6
CH2OH
D-fructose (linear) α-D-fructofuranose
K,
K,

20. 6 CH2OH 6 CH2OH
5 O 5 O
H H H OH
H H
4 H 1 4 H 1
OH OH
OH OH OH H
3 2 3 2
H OH H OH
α-D-glucose β-D-glucose
d α β
,
K,
α K,
β K,

21. H OH H OH
4 6 H O H O
HO 5 HO
HO 2 H HO OH
3 H OH 1 H OH
H OH H H
α-D-glucopyranose β-D-glucopyranose
d
,

22. H H
H H C O C O
C O C O HO C H HO C H
H C OH OH C H HO C H HO C H
H C OH OH C H H C OH HO C H
CH 2 OH CH 2 OH
H C OH H C OH
these two aldotetroses are enantiomers.
They are stereoisomers that are mirror CH 2 OH CH 2 OH
images of each other
these two aldohexoses are C-4 epimers.
they differ only in the position of the
hydroxyl group on one asymmetric carbon
(carbon 4)

24. W
•
• W
•
•
• Z
• W
• E

25. ^
• Fisher projection: straight chain
representation
• Haworth projection: simple ring in
perspective
• Conformational representation: chair
and boat configurations

26. Z ,
•
O O
•
•

27. Z ,
•
5
O O
4 1 4 1
3 2 3 2

28. Z ,
•
• K,
α β
α β

29. D
• α β
α β
OH
OH
H
β α
OH
H OH

30. D
α
β
–d β
–

31. • D
t
α β
β
t
d
α α
β α
d

32. d
^
/

33. ,

34. •K
•

35. • ' '
d
• ' D
d

36. d

37. • ' D
d
Diastereomers:
CHO CHO
CH OH HO CH
HO CH HO CH
HO CH CH OH
CH OH CH OH
CH2OH CH2OH
D-Galactose D- Mannose

38. • ' D
d
Diastereomers:
CHO CHO
CH OH HO CH
HO CH HO CH
HO CH CH OH
CH OH CH OH
CH2OH CH2OH
D-Galactose D- Mannose

39. • '
, K d
d ^
/
Structural isomers:
CHO CH2OH
CH OH CO
HO CH HO CH
CH OH CH OH
CH OH CH OH
CH2OH CH2OH
D-Glucose D-Fructose

40. ^
COOH CHO
CH2OH
H C OH H C OH
H C OH
HO C H HO C H
H C OH
H C OH H C OH
H C OH
H C OH H C OH
CH2OH
CH2OH COOH
D-ribitol
D-gluconic acid D-glucuronic acid
K,

41. ^
CH2OH CH2OH
H O H H O H
H H
OH H OH H
OH OH OH O OH
H NH2 H N C CH3
H
α-D-glucosamine α-D-N-acetylglucosamine
d E

42. O H
H3C C NH O COO−
R HC OH
H H R=
HC OH
H OH
CH2OH
OH H
N-acetylneuraminate (sialic acid)
E E
^
,

43. '
d
R-OH + HO-R' R-O-R' + H2O
K,
H OH H OH
H O H2O H O
HO HO
HO H + CH3-OH HO H
H OH H OH
H OH H OCH3
α-D-glucopyranose methanol methyl-α-D-glucopyranose

44. 6 CH 2OH 6 CH 2OH
5 O 5 O
H H H H
D 4
H
OH H 1 4
H
OH H 1
OH O OH
3 2 3 2
H OH maltose H OH
α → 6 CH 2OH 6 CH 2OH
5
H O H
5 O OH
H H
K, 4
OH H 1 O 4
OH H 1
α OH H H
/ 3 2 3 2
H OH
K cellobiose
H OH
β K
d β →

45. K
^
α K α →
d α → β
β → K,
/ β → α

46. ^
• α β
• β α
•
•
•
•

47. ^
^

48. ^

49. • β α− β
•
• β
α
•

51. D
• α
•
•
• ,

53. • β
•
• '/
•
•

55. CH2OH 6CH OH CH2OH CH2OH CH2OH
2
O 5 O H O H O H H O H
H H H H H
H H H H H
OH H 1 4 OH H 1 OH H OH H OH H
O O O O OH
OH 2
3
H OH H OH H OH H OH H OH
amylose
W
W
'
α →
d

56. CH2OH CH2OH
H O H H O H amylopectin
H H
OH H OH H 1
O
OH
O
H OH H OH
CH2OH CH2OH 6 CH2 CH2OH CH2OH
H O H H O H H 5 O H H O H H O H
H H H H H
OH H OH H OH H 1 4 OH H OH H
4 O O
O O OH
OH
3 2
H OH H OH H OH H OH H OH
α →
α →
d

57. CH2OH CH2OH
H O O
glycogen
H H H
H H
OH H OH H 1
O
OH
O
H OH H OH
CH2OH CH2OH 6 CH2 CH2OH CH2OH
H O H H O H H 5 O H H O H H O H
H H H H H
OH H OH H OH H 1 4 OH H OH H
4 O O
O O OH
OH 2
3
H OH H OH H OH H OH H OH
'
α →
d
d

58. CH2OH 6CH OH CH2OH CH2OH CH2OH
2
O 5 O O H O H O OH
H H H
H H H H H
OH H 1 O 4 OH H 1 O OH H O OH H O OH H
OH H H H
H 2 H
3
H OH H OH H OH H OH H OH
cellulose
β →
β
d ,
t
Schematic of arrangement of
cellulose chains in a microfibril.

59. CH2OH 6CH OH CH2OH CH2OH CH2OH
2
O 5 O O H O H O OH
H H H
H H H H H
OH H 1 O 4 OH H 1 O OH H O OH H O OH H
OH H H H
H 2 H
3
H OH H OH H OH H OH H OH
cellulose
•D ^
•d
•d
K

60. W
•
•
•
• Dt
• t
•
•
•

61. ^
•
• α−
•

63. /

65. • W β β
• z
• W
• D
•
• t
• '
• ,

66. ^

67. W
• D
• D
• K
• ^
•
•
• E

69. '
•
•
• Dt
• α α
•
•
• α β

70. /
• β
•
• :
•
•
•
•

71. •
•
•

72. •
• W
•

73. •
• α α α
• Dt
•
•
•

74. •
•
•
•

76. '
•
•
K
•
•
•

77. '
/

78. '

79. ,
•
–, ^
•
,
DK s

81. '

83. '
•
•
•

84. '

85. ^

87. '

88. W^
'
W^

89. d
d

90. D

91. CH2OH
D-glucuronate 6
− H 5 O
6COO H
4 1 O
O H
H 5
H OH H
4 H 1 3 2
OH
H H NHCOCH3
3 2 O
H OH N-acetyl-D-glucosamine
hyaluronate
'
d
'

92. CH2OH
D-glucuronate 6
− H 5 O
6COO H
4 1 O
O H
H 5
H OH H
4 H 1 3 2
OH
H H NHCOCH3
3 2 O
H OH N-acetyl-D-glucosamine
hyaluronate
,
E
d β → β →

93. heparan sulfate
core glycosaminoglycan
D D protein
transmembrane
α-helix
cytosol
W
d

94. ^
D
s
CH2OH
D-glucuronate 6
− H 5 O
6COO H
4 1 O
O H
H 5
H OH H
4 H 1 3 2
OH
H H NHCOCH3
3 2 O
H OH N-acetyl-D-glucosamine
hyaluronate

95. iduronate-2-sulfate N-sulfo-glucosamine-6-sulfate
H CH2OSO3−
H O H O H
COO− H
OH H O OH H
H O
H OSO3− H NHSO3−
heparin or heparan sulfate - examples of residues
,
E
E
, Ed/ s/Z

96. PDB 1RID
,
t
heparin: (IDS-SGN)5
,
C O N S

97. heparan sulfate
^ core glycosaminoglycan
protein
transmembrane
α-helix
cytosol
d
α
d

98. W
Z ^
iduronate-2-sulfate N-sulfo-glucosamine-6-sulfate
H CH2OSO3−
H O H O H
COO− H
OH H O OH H
H O
H OSO3− H NHSO3−
heparin or heparan sulfate - examples of residues

99. ^

100. K CH2OH C O
H O O CH2 CH
H NH serine
OH H residue
OH O H
H HN C CH3
β-D-N-acetylglucosamine
K
d
K,
K

101. K
• d
• d
• W
• ,

102. ,

104. ^

105. ^

106. ^

107. K

108. CH2OH C O
H O O CH2 CH
H NH serine
OH H residue
OH O H
H HN C CH3
β-D-N-acetylglucosamine
•E ' E K
•D
' E
•K ' E K,

109. CH2OH O HN
H O HN C CH2 CH Asn
H
H C O
OH
H HN
OH
HC R X
H HN C CH3
C O
O
N-acetylglucosamine HN
Initial sugar in N-linked HC R Ser or Thr
glycoprotein oligosaccharide C O
E
E
E

110. d
Z ,K

111. D D
/