Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Experiment Videos

A cleavage method which minimizes side reactions following Fmoc solid phase peptide synthesis.

D S King1, C G Fields, G B Fields

  • 1Department of Molecular and Cell Biology, University of California, Berkeley.

International Journal of Peptide and Protein Research
|September 1, 1990
PubMed
Summary

This study investigated scavengers to prevent side reactions during solid phase peptide synthesis. Reagent K, a specific TFA cleavage mixture, proved highly effective in protecting sensitive amino acids and enabling complex peptide synthesis.

Related Concept Videos

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Effects of Reduced Training on Muscular Power in Swimmers.

The Physician and sportsmedicine·2016
Same author

A-Z of nutritional supplements: dietary supplements, sports nutrition foods and ergogenic aids for health and performance-Part 34.

British journal of sports medicine·2012
Same author

Non-Tuberculous Miliary Lesions of the Lung.

Transactions of the American Clinical and Climatological Association·2011
Same author

Can We Cure Tuberculosis by Cutting Out the Necrotic Foci.

Transactions of the American Clinical and Climatological Association·2011
Same author

Adenoma of bronchus; clinicopathological exercises.

The New England journal of medicine·2010
Same author

Diseases of the lungs; differential diagnosis and treatment.

The Medical clinics of North America·2010

Area of Science:

  • Organic Chemistry
  • Biochemistry
  • Peptide Synthesis

Background:

  • Solid phase peptide synthesis (SPPS) using 9-fluorenylmethoxycarbonyl (Fmoc) amino acids is crucial for peptide production.
  • Deleterious side reactions during trifluoroacetic acid (TFA) cleavage and deprotection limit SPPS success.
  • Susceptible residues like Trp, Tyr, Met, and Cys are prone to modification by TFA-generated protecting groups.

Purpose of the Study:

  • To evaluate the efficacy of various scavengers in mitigating side reactions during Fmoc-SPPS.
  • To identify an optimal cleavage cocktail for minimizing peptide modification.

Main Methods:

  • Comparative analysis of different scavenger combinations in TFA cleavage mixtures.
  • Synthesis and cleavage of ten complex peptides (20-50 residues) using Fmoc chemistry.

Related Experiment Videos

  • Assessment of side reaction inhibition through analytical methods (not detailed in abstract).

    • Main Results:

    • A specific TFA cleavage mixture, Reagent K (82.5% TFA : 5% phenol : 5% H2O : 5% thioanisole : 2.5% EDT), demonstrated maximal efficiency.
    • Reagent K effectively inhibited a wide range of side reactions affecting sensitive amino acid residues.
    • The combination of Fmoc chemistry and Reagent K facilitated efficient synthesis of complex peptides.

    Conclusions:

    • Reagent K is a superior scavenger cocktail for Fmoc-SPPS, significantly reducing side reactions.
    • This optimized cleavage protocol enhances the reliability and efficiency of synthesizing complex peptides.
    • Fmoc chemistry is highly compatible with Reagent K for advanced peptide synthesis applications.