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Related Experiment Videos

Asparagine coupling in Fmoc solid phase peptide synthesis.

H Gausepohl1, M Kraft, R W Frank

  • 1European Molecular Biology Laboratory, Heidelberg, West Germany.

International Journal of Peptide and Protein Research
|October 1, 1989
PubMed
Summary
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Side chain unprotected asparagine in peptide synthesis can dehydrate to beta-cyano alanine. Using Fmoc-Asn-OPfp or protected derivatives with BOP coupling avoids this, but protection groups can alkylate tryptophan.

Area of Science:

  • Peptide Chemistry
  • Organic Synthesis

Background:

  • Solid-phase peptide synthesis (SPPS) is crucial for creating peptides.
  • Side chain unprotected asparagine (Asn) can undergo dehydration during activation, forming beta-cyano alanine.
  • This side reaction complicates peptide synthesis and purification.

Purpose of the Study:

  • To investigate and identify side reactions during the activation of side chain unprotected asparagine in Fmoc-SPPS.
  • To evaluate different coupling conditions and protecting groups for asparagine introduction.
  • To develop optimized strategies for synthesizing homogeneous peptides containing asparagine and tryptophan.

Main Methods:

  • Synthesis of Met-Lys-Asn-Val-Pro-Glu-Pro-Ser using various asparagine activation methods (DCC/HOBt, BOP, pentafluorophenyl ester).

Related Experiment Videos

  • Analysis of crude peptide products using High-Performance Liquid Chromatography (HPLC), mass spectrometry, and Edman degradation.
  • Evaluation of side chain protected asparagine derivatives (Fmoc-Asn(Mbh)-OH, Fmoc-Asn(Tmob)-OH) and Fmoc-Asn-OPfp.

    • Main Results:

    • Dehydration of unprotected Fmoc-asparagine during carboxyl activation led to beta-cyano alanine formation.
    • Homogeneous peptides were obtained using Fmoc-Asn-OPfp or BOP-mediated activation with side chain protected asparagine.
    • Mbh and Tmob protecting groups, while efficient for coupling, generated carbonium ions during acidolytic cleavage, alkylating tryptophan residues.

    Conclusions:

    • Coupling of Fmoc-Asn-OPfp is a reliable method to avoid beta-cyano alanine formation.
    • Side chain protection for asparagine can lead to tryptophan alkylation during cleavage; scavengers can mitigate this.
    • Optimized strategies are necessary for synthesizing homogeneous peptides containing both asparagine and tryptophan.