Is it possible for basic amino acids like arginine and histidine to undergo a do

Question

Is it possible for basic amino acids like arginine and histidine to undergo a double protonation at low enough PH's like around 2?

The first pKa of argine is 12.5 and histidine is 6.0. I'm not sure what their second pKa value would be.

Argine is :                                                                        Histidine is:

R-CH2CH2CH2-NH - C = NH                                       NH+

                                         |                                               / /       

                                        N                                          HC         CH

                                                                                           ___//

                                                                                     HN         

                                                                                                     C-R

Explanation / Answer

second pKa values for them will be around 2 and 9.. which is possible at low PH

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