H₂NOOHOH
Polar, uncharged

Threonine

Thr · T · 119.12 Da

EssentialGlucogenic and ketogenicHydroxyl-containing Essential

Hydroxyl (secondary alcohol)

Like isoleucine, branched at Cβ with two chiral centers. Both a phosphorylation site and an O-glycosylation anchor.

Mnemonic
T for Threonine, serine plus a methyl, so it is the branched alcohol.

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

pI = (2.11 + 9.62) / 2 = 5.86, 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.