[peptideismylife]

Hi guys,

I have some peptides with Lysines residues that are protected with Alloc. I was wondering whether then the lone pair of the resulting secondary amine is more nucleophilic or less nucleophilic. Since what we formed is a carbamate (R-NH-CO-O-CH2=CH2), I would say that the lone pair on the nitrogen is less nucleophilic because we can delocalize it on the carbamate. But what make me feel confused is that Alloc group containg an electron donating group such an alkene which could make the lone pair more nucleophilic...

Any suggestion?

[discodermolide]

The NH of carbamates is generally less nucleophillic.