Converting format

All the music on my Mac is in Apple Lossless format and consequently it occupies huge amounts of disk space. In order to increase the number of tracks I can get onto my lovely new nano, I would like to automatically convert files to a a more compressed format when they are being transferred. Is this possible?
If I have to do the conversion manually on the Mac before transferring to the nano, how do I organise things within iTunes to ensure it transfers the compressed files rather than the lossless ones?

This feature is only supported on the iPod Shuffle unfortunately. If you do duplicate songs in iTunes for both formats, I think you can sort your music on format type. I might be wrong and I can't check since I'm at work and don't have access to iTunes.
Glor

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