(3-Formylindolyl)acetamidomethyl polystyrene

Description

• General description: Versatile indole-based linker for the synthesis of secondary amides, carbamates, ureas [1,2,3,4] and aminopurines [5]. In a study comparing the cleavage rates of secondary amides, ureas, carbamates and sulfonamides from indole, dialkoxybenzaldehyde and Rink amide resins, the indole resin was found to be the most acid-labile [6].Reductive amination with excess of amine and NaBH(OAc)3 in DCE/TMOF [seepage], NaBH3CN in THF/TMOF/AcOH, or NaBH4-Ti(OiPr)4 in THF [2], converts the formyl group to the appropriate secondary amine. Cleavage can be effected with 2-5% TFA in DCM, depending on the nature of the product being released from the resin. Associated Protocols and Technical Articles Protocols for Loading of Peptide Synthesis Resins Literature references[1] K. G. Estep, et al. (1998) J. Org. Chem., 63, 5300. [2] S. Bhattacharyya, et al. (2003) Tetrahedron Lett., 44, 6099. [3] N. Hone, et al. (2003) Tetrahedron Lett., 44, 8169. [4] L. Sereni, et al. (2004) Tetrahedron, 60, 8561. [5] P. H. Dorff and R. S. Garigipati (2001) Tetrahedron Lett., 42, 2771. [6] B. Yan, et al. (2000) J. Comb. Chem., 2, 66.
• Linkage: Replaces: 01-64-0361
• Analysis Note: Color (visual): white to yellow to beigeAppearance of substance (visual): beadsLoading (determined by elemental analysis of sulfur after coupling with tosylhydrazide): 0.60 - 1.20 mmol/gSwelling Volume (in DMF): lot specific resultThe polymer matrix is copoly (styrene-1% DVB), 100 - 200 mesh
• Legal Information: Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany