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Related Experiment Videos

The aspartimide problem in Fmoc-based SPPS. Part III.

M Mergler1, F Dick

  • 1Bachem AG, Hauptstr. 144, CH-4416 Bubendorf, Switzerland.

Journal of Peptide Science : an Official Publication of the European Peptide Society
|April 26, 2005
PubMed
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A new Fmoc-Asp derivative effectively minimizes aspartimide by-products during solid-phase peptide synthesis (SPPS). This advancement is crucial for producing complex peptides and improving synthesis efficiency.

Area of Science:

  • Organic Chemistry
  • Peptide Chemistry
  • Biochemistry

Background:

  • Aspartimide formation is a common side reaction in Fmoc-based solid-phase peptide synthesis (SPPS).
  • This side reaction leads to the formation of by-products, complicating purification and reducing yield.
  • Protecting group strategies for aspartic acid are critical for mitigating this issue.

Purpose of the Study:

  • To evaluate a newly developed Fmoc-Asp derivative, Fmoc-Asp beta-(2,3,4-trimethyl-pent-3-yl) ester, for its efficacy in reducing aspartimide formation.
  • To compare the performance of this new derivative against other protecting groups, including Asp(OMpe) and the standard Asp(OtBu).
  • To assess the impact of base exposure duration on by-product formation.

Main Methods:

  • Solid-phase peptide synthesis (SPPS) using the Fmoc strategy.

Related Experiment Videos

  • Incorporation of a hexapeptide model (H-Val-Lys-Asp-Xaa-Tyr-Ile-OH) with various amino acids at the Xaa position.
  • Systematic variation of the aspartic acid beta-carboxy protecting group and exposure time to bases like piperidine and DBU.

    • Main Results:

    • The new Fmoc-Asp derivative significantly reduced aspartimide by-product formation compared to Asp(OMpe) and Asp(OtBu).
    • Improved results were observed with prolonged exposure to bases when using the new derivative.
    • The new protecting group demonstrated superior performance, particularly for challenging peptide sequences.

    Conclusions:

    • The novel Fmoc-Asp beta-(2,3,4-trimethyl-pent-3-yl) ester is highly effective in suppressing aspartimide formation during SPPS.
    • This derivative offers enhanced stability and is valuable for synthesizing long or complex peptides.
    • The findings provide a more robust method for peptide synthesis, minimizing critical side reactions.