Iphone 3gs wont sync with music or video on itunes on mac but will on pc

All software is up to date but my IMAC has stopped syncing music and video to my iphone 3gs.
The phone will sync fine on a windows pc but I prefer to use the IMAC photos don't appear to be an issue
Running Itunes 10.2.2

A little note to add to the confusion with this is my wife's Iphone4 syncs fine with Imac and Pc

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