Master of Science
Department of Chemistry
Abdipranoto, Albertus A., The application of ketimine derivatives in solid phase peptide synthesis, Master of Science thesis, Department of Chemistry, University of Wollongong, 1978. http://ro.uow.edu.au/theses/2632
The N- [a-phenyl-(5-substituted-2-hydroxybenzylidene)] -amino acids react smoothly with amino acyl polymers in the presence of N,N'-dicyclohexylcarbodiimide (DCC) to afford the ketimine peptide resin esters in quantitative yield. Several N-protected dipeptide resin esters were synthesized and characterized as their methyl ester derivatives. The ketimine protecting group was found to be remarkably stable to hydrolysis when incorporated into a Merrifield resin, in fact no suitable method for its removal from peptide resins could be developed. This unusual stability of the diarylmethylene protecting group when incorporated into a Merrifield type styrene divinylbenzene polymer support suggested its suitability for the side chain protection of ornithine and lysine in solid phase peptide synthesis.