An audiobook will not sync with my iPod

I bought an audiobook from iTunes about 2 years ago. It was on my iPod and played perfectly all that time.
About two weeks ago I noticed that all my audiobooks had disappeared from both the iPod and the iTunes library on the PC. I have manged to get them all back onto the computer and most of them are synced back onto my iPod too.
However, this one just will not sync and I cannot listen to it on the iPod anymore. It appears in the list of available books, I ticked it, but it won't sync.
When I click on the Device in the sidebar of iTunes and click on  Books the name of the audiobook there in the list, but it is in grey type, not black, and there is a little circle of dots in the left hand column, just after the number.
It looks as if some of it has synced, but not the whole thing.
Any ideas? iPod support were no help and iTunes support wanted to charge me £25 for a problem they seem to have created!!

What happens when you try to sync your Shuffle with iTunes?  Do you get any error messages? Does the Shuffle even appear in your iTunes library?
A little more detail would be a lot of help.
B-rock

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