Maleic anhydride or Itaconic anhydride for amino group protection?

WS via (by novalidaddress from
Sun Apr 11 17:16:14 EST 2010

Dear experts,

I want to reversibly protect an amino group in a quite sensitive
molecule, in a reaction in the gram scale. I came across maleic
anhydride and itaconic (methylmaleic) anhydride. Any ideas which one
is more convenient to use (and to get rid of)? Is there a major
difference between them, actually? Both are introduced in alkaline
conditions (pH 9) and removed with a not too acidic buffer (pH 3)

Many thanks for your suggestions!


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