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Acting as either an acid or a base

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Some substances can’t make up their minds about what they are; they can act as either an acid or a base. Chemists classify these substances as amphiprotic or amphoteric substances. For example, the bicarbonate ion can act as either an acid or a base:

 

 

Biochemically important molecules may also exhibit amphiprotic behavior. Amino acids contain both a basic amine group and an acidic carboxyl group. Therefore, they can act as either acids or bases. For example, glycine may undergo the following reactions:

 

 

In fact, amino acids may undergo proton transfer from the carboxyl end to the amine end, forming an overall neutral species that has a positive and negative end. Species such as these are called zwitterions (not to be confused with twitterions — people who tweet until their thumbs fall off):


Biochemistry For Dummies

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