1935981-35-3

White crystalline powder

Fmoc-Aeg(N3)-OH is a click chemistry reagent containing an Azide. Alkylating the Nitrogen of an amide bond results in peptoid structures, which leads to conformational restrains, like N-methylation and allows backbone derivatisation. Altering cytotoxicity, bacterial cell selectivity and receptor pharmacology through formation of peptoid derivatives have been published for Cilengitide, Piscidin 1, and MC3, MC4 and MC5 receptor agonist. This building block enables design of macrocycles through intermolecular crosslinking or backbone stabilization through intermolecular ring-closure. This compound is a potential building block for the construction of (customized) peptide nucleic acids (PNAs) and for peptoid synthesis[1]. Fmoc-Aeg(N3)-OH is a click chemistry reagent, it contains an Azide group and can undergo copper-catalyzed azide-alkyne cycloaddition reaction (CuAAc) with molecules containing Alkyne groups. It can also undergo strain-promoted alkyne-azide cycloaddition (SPAAC) reactions with molecules containing DBCO or BCN groups.

[1] Fernández-Llamazares AI, et al. The backbone N-(4-azidobutyl) linker for the preparation of peptide chimera. Org Lett. 2013 Sep 6;15(17):4572-5. DOI:10.1021/ol402150m
[2] Kruijtzer JA, et al. Peptoid-peptide hybrids as potent novel melanocortin receptor ligands. J Med Chem. 2005 Jun 30;48(13):4224-30. DOI:10.1021/jm0490033
[3] Kim JK, et al. Structural flexibility and the positive charges are the key factors in bacterial cell selectivity and membrane penetration of peptoid-substituted analog of Piscidin 1. Biochim Biophys Acta. 2010 Oct;1798(10):1913-25. DOI:10.1016/j.bbamem.2010.06.026