Poster Presentation 6th Modern Solid Phase Peptide Synthesis & Its Applications Symposium 2017

Convenient method of peptide hydrazide synthesis using a new hydrazone resin (#64)

Nicol Haasmann 1 , Pavel Chelushkin 2 , Ksenia Polyanichko 2 , Maria Leko 2 , Marina Dorosh 2 , Thomas Bruckdorfer 2 , Sergey Burov 2
  1. Iris Biotech GmbH, Marktredwitz, Germany
  2. St Petersburg State University, St Petersburg, Russia

Peptide hydrazides can be easily synthesized using a new hydrazone resin obtained via acylation of aminomethyl polystyrene by Fmoc-hydrazone of pyruvic acid. It was shown that the hydrazone linker is completely stable in the course of standard Fmoc-SPPS. Moreover, it can tolerate a treatment with 5% TFA/DCM thus permitting selective removal of Mtt or related acid-labile protecting groups. Subsequent application of cleavage cocktails containing neat TFA permist obtaining the peptide in reasonable yields and purity. Synthesized peptide hydrazides can be applied as building blocks for the conjugation with different carrier molecules using hydrazone ligation techniques.