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Please use this identifier to cite or link to this item: http://hdl.handle.net/1807/33912

Title: Reactivity of Aziridine Aldehyde Dimers and their Utility in the Synthesis of Peptidomimetics
Authors: Assem, Naila Magdy
Advisor: Yudin, Andrei
Department: Chemistry
Keywords: peptide
ligation
amino aldehyde
Issue Date: 6-Dec-2012
Abstract: Amino aldehydes are important building blocks in organic synthesis. However, due to the innate propensity for condensation to occur upon combination of aldehydes and amines, uprotected amino aldehydes are unstable. One exception to this is the existence of dimeric aziridine aldehydes. We have shown that the enhanced stability observed with these unprotected aziridine aldehydes is due to their dimeric nature. In addition, we have shown that reversible dimer dissociation plays a key role in the kinetics and stereoselectivity of subsequent reactions. Reductive amination with the unprotected amino aldehyde dimers occurs without double addition or epimerization. The resulting aziridine conjugates were used towards a convergent synthesis of aminomethylene peptidomimetics, by aziridine ring opening with C-terminal peptide thioacids. We have shown that we can also utilize the aziridine aldehydes towards the assembly of branched peptides.
URI: http://hdl.handle.net/1807/33912
Appears in Collections:Doctoral

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