Purchases made on my ipod touch are no longer being transferred to the Mac...but yet they are showing up in "grey" in the purchased list on the Mac.  Any clues as to what is going on?

What used to work just fine, is no longer working...
Within the last 2 days, song purchases that were made on my ipod Touch are no longer being transferred when the ipod synchs up.  The strange thing is that the songs appear in iTunes --> Store -- Purchased list, but are greyed out.  They play just fine on the ipod...but aren't making it back to the Mac.
I have tried right clicking on the ipod when it appears in iTunes and selecting "Transfer purchases", but that doesn't seem to work either.
Any clues as to what is going on?
Thanks,
Tim

One other very important piece of information I forgot to include...the purchases were made prior the iOS update.  So the sequence of events went like this:
1) ipod Touch with previous iOS (4.0 I think)
2) purchases made
3) ipod connected and iTunes prompts for iOS update
4) iOS upgraded to 5.0
5) Now the purchases seem to be stranded on the ipod Touch
Thanks!

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