Description

• General description: A useful tool for the synthesis of branched, side-chain modified and cyclic peptides and peptide tools for click chemistry by Fmoc SPPS. The side-chain azido group is completely stable to piperidine and TFA, but can be readily converted to an amine on the solid phase or in solution by reduction with thiols [1] or phosphines. [2],[3] Associated Protocols and Technical Articles Cleavage and Deprotection Protocols for Fmoc SPPS Guide to Selection of Orthogonally-Protected Building Blocks for Fmoc SPPS Literature references: [1] M. Meldal, et al. (1997) Tetrahedron Lett., 38, 2531. [2] J. T. Lundquist & J. C. Pelletier (2001) Org. Lett., 3, 781. [3] N. Nepomniaschiy, et al. (2008) Org. Lett., 10, 5243.
• Application: Recent applications of Fmoc-azidolysine include:In the synthesis of a cationic cell-penetrating peptide (CPP) by click-chemistry.[4]In the preparation of a peptide-resorcinarene conjugate by click chemistry.[5]
• Analysis Note: Colour (visual): white to slight yellow to beigeAppearance of substance (visual): powderIdentity (IR): passes testAssay (HPLC, area%): ≥ 98.0 % (a/a)Solubility (1 mmole in 2 ml DMF): clearly soluble
• Legal Information: Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany