Synthesis of polyamines and polyamine toxins. An improved alkylation procedure

Polyamines and polyamine toxins are biologically important molecules, having modulatory effects on nucleotides and proteins. Here we present an improved alkylation procedure, which allows sequential synthesis of polyamines and polyamine toxins on solid phase using N-protected aminoalkyl halides and 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) as base. The feasibility of the procedure is demonstrated with the synthesis of the native polyamine toxin, PhTX-433, as well as an analogue, PhTX-56, which is a very potent and subtype selective glutamate receptor antagonist.