(3-Formylindolyl)acetamidomethyl polystyrene

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.

Replaces: 01-64-0361

Color (visual): white to yellow to beige
Appearance of substance (visual): beads
Loading (determined by elemental analysis of sulfur after coupling with tosylhydrazide): 0.60 - 1.20 mmol/g
Swelling Volume (in DMF): lot specific result
The polymer matrix is copoly (styrene-1% DVB), 100 - 200 mesh

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