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Maltose

Maltose is a disaccharide composed of two D-glucose molecules linked by an α-1,4-glycosidic bond. It is produced by the hydrolysis of starch and is found in both α and β forms. Structural elucidation of maltose showed that it is a reducing sugar that yields two molecules of D-glucose upon hydrolysis. Methylation and degradation experiments revealed that one glucose residue is in a hemiacetal form, with C-1, C-2, C-3 and C-4 free, while the other glucose is linked via C-4, indicating an α-1,4-glycosidic linkage. Maltose exhibits mut

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159 views13 pages

Maltose

Maltose is a disaccharide composed of two D-glucose molecules linked by an α-1,4-glycosidic bond. It is produced by the hydrolysis of starch and is found in both α and β forms. Structural elucidation of maltose showed that it is a reducing sugar that yields two molecules of D-glucose upon hydrolysis. Methylation and degradation experiments revealed that one glucose residue is in a hemiacetal form, with C-1, C-2, C-3 and C-4 free, while the other glucose is linked via C-4, indicating an α-1,4-glycosidic linkage. Maltose exhibits mut

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STRUCTURAL

ELUCIDATION
OF MALTOSE
Disaccharides
• Disaccharides are composed of two monosaccharide units

• Common disaccharides are Sucrose, Lactose and Maltose.


• The formula of these disaccharides is C12H22O11

• Classified into non


non--reducing such as sucrose and reducing such as
maltose and lactose
lactose..
• One molecule of disaccharide on hydrolysis yields two molecules
of monosaccharide
monosaccharide.. The disaccharide arise formally by
intermolecular dehydration between two monosaccharide
molecules e.g. ,

C6H12O6 + C6H12O6 C12H22O11 + H2O


Hexose Hexose Disaccharide
 Also known as Malt sugar.
sugar.
 Composed of two D-glucose Maltose
molecules.
 Obtained from the hydrolysis of
starch.
 Linked by an -1,4
1,4--glycosidic
bond.
 Found in both the - and β -
forms.
 Maltose is a white crystalline
solid M.p
M.p.. 160 – 165 C .
 Soluble in water and is
Dextrorotatory
 Reducing sugar.
 Its glycosidic linkage is acid
labile 4
Maltose

CH2OH CH2OH
O O OH

OH OH
O
OH
OH OH
 -1,4
1,4--glycosidic bond
- D-Maltose
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Structural elucidation of Maltose
 Molecular formula C12H22O11
 Reducing sugar-
sugar-reduces Benedict`s,Tollen`s and
Fehling`s reagents
 With phenylhydrazine form an osazone having the
formula C12H20O9(=NNHC6H5)2
 With bromine water , maltose is oxidised to a
monocarboxylic acid which is (C11H21O10)COOH called
Maltonic Acid .
 Exhibits Mutarotation
 Maltose is hydrolysed in aqueous acid or when treated with the
enzyme maltase (from yeast) it yields two moles of D-
D-glucose .
This reaction reveals that maltose is made up of two D-
D-glucose
units which are joined together by the loss of one molecule of
water:

2 C6H12O6 - H2O  C12H22O11

 Hydrolysis by acid to yield a new reducing group (two reducing


D-glucose molecules in place of one maltose molecule ) is
characteristic of glycosides . Thus one of the glucose residues
of maltose is present in a hemiacetal form & other must be
present as a glucoside . The configuration of this glucosidic
linkage can be inferred as because maltose is hydrolysed by
-glucosidases & not by  glucosidases .
 Methylation of maltonic acid followed by hydrolysis with HCl
yields 2 ,3,4,6-
,3,4,6-tetra
tetra--O-methyl-
methyl-D-glucose & 2,3,5,6
2,3,5,6--tetra
tetra--O-
methyl--D-gluconic acid .
methyl

 When methylation of maltose is done followed by hydrolysis , it


yields 2,3,4,6-
2,3,4,6-tetra
tetra--O-methyl-
methyl-D-glucose & 2,3,6
2,3,6--tri-
tri-O-methyl
methyl--
D-glucose .
Facts Behind the Maltose (I) Structure
 Occurance of specific rotation of Maltose which confirms the α-glucosidic
linkage .
 C-1 (of the reducing half ) is free & as Maltose forms an osazone , this shows
that C-
C-2 is also free , i.e. , not combined with an alkoxy group .
 Zemplen (1927) degraded maltose by one carbon atom to yield a compound
which still formed an osazone .This shows that C C--3 is free . He further
degraded this by one carbon atom to yield a compound which did not forman
osazone , indicating that C C--4 in maltose is not free & is thus involved in
glycosidic linkage .
Conformation of Structure (I) via synthesis.
• Presence of free –CHOH in Maltose causes it to exist in two
different Anomeric forms - and .
• Mutarotation
• It undergoes mutarotation, specific rotation -maltose +168 and
-maltose +112 and +136 for equilibrium mixture.

12
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