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Sigma-Aldrich

(3-Formylindolyl)acetamidomethyl polystyrene

Novabiochem®

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Quality Level

product line

Novabiochem®

form

beads

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

functional group

aldehyde

storage temp.

2-8°C

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 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

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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