H₂NOOHONH₂
Polar, uncharged

Glutamine

Gln · Q · 146.15 Da

Non-essential

Amide

Amide of glutamate, one carbon longer than asparagine. The main nitrogen shuttle in blood.

Mnemonic
Q-tamine. "Gln" sounds like Q, the spare letter next to N.

Ionization ladder
pKaGroupChangeCharge
2.17 α-carboxyl -COOH → -COO⁻ 0 → −1
9.13 α-amino -NH₃⁺ → -NH₂ +1 → 0

pI = (2.17 + 9.13) / 2 = 5.65, the midpoint of the two pKa values that bracket the neutral species.

Net charge across pH
pH 1+1
pH 40
pH 70
pH 10−1
pH 13−1

A group is deprotonated once the pH climbs past its pKa. Add the contributions and you have the net charge, with no memorization required.