ChemDraw is a piece of software that attempts to be as intelligent as possible. In many cases, that is truly helpful, in others it can be annoying.

When labelling an atom in text mode, ChemDraw will automagically assume a label from left to write (i.e. in standard North American/European writing direction) and interpret the label as such. If it finds that the atom has bonds to the right but none to the left, as tyrosine’s hydroxy group has in your example, it will group the label into ‘sensible’ fragments^[1] and reverse them. This makes sense if you think of rotating a molecule: If you had drawn tyrosine rotated by $180^\circ$, you would have wanted to add OH on the rightmost atom, not HO. If you then manually rotate the entire molecule within ChemDraw, you will notice the OH flipping into an HO as soon as it graphically makes sense to do so.

Note that if you just hover over the atom in lasso mode or bond adding mode and then hit o (lowercase!) it will automatically add OH (or HO, depending on the orientation) at that position. Hitting o again will remove the additional hydrogen (this holds true for all chemical elements that are attached to single letters regardless whether the atom is attached to a lowercase letter (i.e. o) or an uppercase one (B for boron)).

[1]: Consider OTBS: ChemDraw automatically recognises TBS as an abbreviation for the $\ce{TBS}$ group so when reversing, it becomes TBSO. However ChemDraw does not standardly recognise the triethylsilyl group $\ce{TES}$, so when reversing OTES it arrives at SETO. The preferred way would be to add an abbreviation to ChemDraw.

ChemDraw is a piece of software that attempts to be as intelligent as possible. In many cases, that is truly helpful, in others it can be annoying.

When labelling an atom in text mode, ChemDraw will automagically assume a label from left to right (i.e. in standard North American/European writing direction) and interpret the label as such. If it finds that the atom has bonds to the right but none to the left, as tyrosine’s hydroxy group has in your example, it will group the label into ‘sensible’ fragments^[1] and reverse them. This makes sense if you think of rotating a molecule: If you had drawn tyrosine rotated by $180^\circ$, you would have wanted to add OH on the rightmost atom, not HO. If you then manually rotate the entire molecule within ChemDraw, you will notice the OH flipping into an HO as soon as it graphically makes sense to do so.

Note that if you just hover over the atom in lasso mode or bond adding mode and then hit o (lowercase!) it will automatically add OH (or HO, depending on the orientation) at that position. Hitting o again will remove the additional hydrogen (this holds true for all chemical elements that are attached to single letters regardless whether the atom is attached to a lowercase letter (i.e. o) or an uppercase one (B for boron)).

[1]: Consider OTBS: ChemDraw automatically recognises TBS as an abbreviation for the $\ce{TBS}$ group so when reversing, it becomes TBSO. However ChemDraw does not standardly recognise the triethylsilyl group $\ce{TES}$, so when reversing OTES it arrives at SETO. The preferred way would be to add an abbreviation to ChemDraw.