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Introduction
Classification of Carbohydrates
Chapter22
Light from the sun is absorbed by chlorophyll and this is converted to the energy
Chapter22
Chapter22
Monosaccharides
Classification of Monosaccharides
Chapter22
Chapter22
A Fischer projection cannot be removed from the plane of the paper or turned 90 o
The cyclic hemiacetals differ only in configuration at C1 and are called anomers
The carbon at which their configurations differ is called the anomeric carbon
The -anomer has the C1 hydroxyl trans to the -CH2OH group
The -anomer has the C1 hydroxyl cis to the -CH2OH group
Chapter22
Chapter22
Chapter22
Chapter22
10
Mutarotation
Mutarotation of glucose results in an equilibrium mixture of 36% glucose and 64% -glucose
The more stable -glucose form predominates
Chapter22
11
Chapter22
12
Glycoside Formation
When glucose reacts with methanol in the presence of catalytic acid, the methyl
glycoside is obtained
A glycoside made from glucose is called a glucoside
Chapter22
13
Chapter22
14
Chapter22
15
Chapter22
16
Formation of Ethers
Chapter22
17
Silyl ethers are also used as protecting groups for the hydroxyls of
carbohydrates
Sterically bulky tert-butyldiphenylsilyl chloride (TBDPSCl) reacts selectively at the
Chapter22
18
Conversion to Esters
Chapter22
19
Aldoses and ketoses give positive tests when treated with Tollens
solution or Benedicts reagent
Tollens reagent [Ag(NH3)2OH] gives a silver mirror when Ag+ is reduced to Ag0
Benedicts reagent (an alkaline solution of cupric citrate complex) gives a brick
In basic solution a ketose can be converted to an aldose that can then react with
Chapter22
20
ketone form, which can react with Tollens and Benedicts reagents
Chapter22
21
Dilute nitric acid oxidizes both the aldehyde and primary hydroxyl
groups of an aldose to an aldaric acid
Chapter22
22
Compounds
Chapter22
23
Chapter22
24
Chapter22
25
Phenylhydrazine: Osazones
Chapter22
26
epimers
Chapter22
27
aldoses
Chapter22
28
Chapter22
29
Chapter22
30
Chapter22
31
Disaccharides
Sucrose (Table sugar)
Chapter22
32
Maltose
Cellobiose
Chapter22
33
Polysaccharides
Starch
Chapter22
34
Chapter22
35
Glycogen
The large size of glycogen prevents if from leaving the storage cell
The storage of tens of thousands of glucose molecules into one molecule greatly
relieves the osmotic problem for the storage cell (this would be caused by the
attempted storage of many individual glucose molecules)
The highly branched nature of glycogen allows hydrolytic enzymes to have many
chain ends from which glucose molecules can be hydrolyzed
Long chain fatty acids of triacylglycerols are used for long term energy storage
Chapter22
36
Cellulose
Chapter22
37
Chapter22
38