Gluconic acid, 2-amino-2-deoxy deamination

Deamination of 2-amino-2-deoxyaldonic acids with nitrous acid has been shown to give 2,5-anhydroaldonic acids with overall retention of the configuration of C-2. The reaction parallels the deamination, with nitrous acid, of a-amino acids that leads to a-hydroxy acids with retention of configuration.19,29 Thus, the formation of 2,5-anhydro-D-gluconic acid27 (15) from 2-amino-2-deoxy-D-gluconic acid (14) has... 

Deamination of the methyl ester (19) of 2-amino-2-deoxy-L-gluconic acid with nitrous acid gave methyl 2,5-anhydro-L-... 

Anhydroaldonate derivatives are formed in good yield when 2-amino-2-deoxyaldonic acids are deaminated. Thus, deamination of 2-amino-2-deoxy-L-(and D-)gluconic acid was used to form the tetra-... 

During the deamination of 2-amino-2-deoxy-D-gluconic acid, it is probable that the carboxyl group is involved in a participation reaction with the carbonium cation CVIII from the side of the molecule opposite to the departing diazo group, to give an intermediate CIX with the d-manno con-... 

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