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Cyclic Structure of Glucose – Anomers

 

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We know monosaccharides have cyclic hemiacetal or hemiketal structures. To illustrate, let us first consider the example of D-glucose. During hemiacetal formation C5 – OH of glucose combines with the C1 – aldehydic group. As a result, C1 becomes chiral or asymmetric and thus has two possible arrangements of H and OH groups around it. In other words, D-glucose exists in two stereoisomeric forms, i.e., α-D-glucose and β-D-glucose as shown below:
In α-D-glucose, the OH group at C1 is towards right while in β-D-glucose, the OH group at C1 is towards left. Such a pair of stereoisomers which differ in configuration only around C1 are called anomers and the C1 carbon is called Anomeric carbon (or glycosidic carbon.  The cyclic structures of monosaccharides can be better represented by Haworth Projection formulae. To get such a formula for any monosaccharide (say α-and β-D-glucose), draw a hexagon with its oxygen atom at the upper right hand corner. Place all the groups (on C1, C2, C3 and C4) which are present on left hand side in structures I and II, above the plane of the ring and all those groups on the right hand side below the plane of the ring. 
The terminal – CH2OH group is always placed above the plane of the hexagon ring (in D-series). Following the above procedure, Haworth Projection Formulae for α-D-glucose (I) and β-D-glucose (II) are obtained as shown below:

 

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