Recently IBM Watson demonstrated the effectiveness of a natural language question answering algorithm. Of course, beyond the game of Jeopardy, this problem becomes more difficult. The accumulated body of mathematical knowledge seems to be a good target for domain specific natural language question answering algorithms, something like an automated Math Overflow. Is this being pursued?
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I do not know whether there is anyone pursuing this, but I believe that there should be. All LaTeX files on the arxiv are publicly visible, and of course they contain richly structured markup with crossreferences between different parts of the same document and links to other documents. MathSciNet and Zentralblatt also have a lot of richly structured data. I think that a Watsonlike system could digest enough of this to give much better answers to certain types of questions than current search engines can. I don't think you could expect to provide actual answers to mathematical questions, but I think you could do a good job of pointing people to papers where answers could be found. 

