General Chemistry of 2-Amino-2-deoxy-D-glucose

General Chemistry of 2-Amino-2-deoxy-d-glucose 1. Acyl Derivatives 

Peracylation can be achieved by treatment of the amino sugar with the appropriate acid anhydride or chloride in pyridine at room temperature87 or with the acid anhydride and the sodium salt of the acid at a higher temperature88 the resulting product is usually a mixture of the a and 0 anomers 

2-Acetamido-2-deoxy-D-glucose derivatives generally crystallize as the a anomer and mutarotate in polar solvents to a mixture of the two anomers, but the pure /3 anomer may be prepared by acylation of 2-amino-2-deoxy-(3-n-glucose at a low temperature with the acid anhydrides in A, A-dimeth-ylformamide solution.100 Mutarotation in this solvent is very slow, and the reaction product may be removed long before mutarotational equilibrium has been established. 

It has been known for some time that A-acetyl derivatives of amino sugars may be obtained enzymically.101103 Synthetic A-acyl derivatives obtained by using aromatic acids104 act as competitive inhibitors for hexo-kinase. 

The reaction of phthalic anhydride with 1,3,4,6-tetra-0-acetyl-2-amino-2-deoxy-D-glucose leads to the formation of the expected A-phthaloyl amide or phthalamic acid. Furthermore, intramolecular condensation occurs, presumably by way of a mixed anhydride intermediate, on treating this with ethyl chloroformate, thereby forming an A,A-phthaloyl imide, 1,3,4,6-tetra-0-acetyl-2-deoxy-2-phthalimido-D-glucose.105 106 The 2-amino-2-deoxy-D-glucose derivative can be regenerated by the action of hydrazine.69 107 

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