Word Pro for OS/2 suffers from the problem that it only supports codepage 850. As a result, typographic quotation marks, or curly quotes, are unavailable. I have modified some fonts by swapping the quotedblleft and quotedblright characters with the guillemotleft and guillemotright characters. Now you can access curly quotes by typing Left-Alt-174 and Left-Alt-175. Here's what they look like:
The problem with this approach is that if you send a document with these fonts somewhere else that doesn't have the modified fonts, then each curly quote will be displayed as a guillemot. If the curly quote is actually available normally on the other system, then it is a simple matter to do a search and replace of the guillemot characters.
Here are some instructions on how to assign a key to the curly quotes.