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

Solution versus solid-phase cyclization strategies for large sidechain lactam-bridged peptides: a comparative study

J A Camarero1, J J Cairó, E Giralt

  • 1Department of Organic Chemistry, University of Barcelona, Spain.

Journal of Peptide Science : an Official Publication of the European Peptide Society
|July 1, 1995
PubMed
Summary
This summary is machine-generated.

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

Brain metastasis models: What should we aim to achieve better treatments?

Advanced drug delivery reviews·2020
Same author

The antiproliferative peptide Ctn[15-34] is active against multidrug-resistant yeasts Candida albicans and Cryptococcus neoformans.

Journal of applied microbiology·2019
Same author

LOXL2-mediated H3K4 oxidation reduces chromatin accessibility in triple-negative breast cancer cells.

Oncogene·2019
Same author

New developments in online OUR monitoring and its application to animal cell cultures.

Applied microbiology and biotechnology·2019
Same author

Effect of continuous feeding of CO<sub>2</sub> and pH in cell concentration and product titers in hIFNγ producing HEK293 cells: Induced metabolic shift for concomitant consumption of glucose and lactate.

Journal of biotechnology·2018
Same author

A new strategy for fed-batch process control of HEK293 cell cultures based on alkali buffer addition monitoring: comparison with O.U.R. dynamic method.

Applied microbiology and biotechnology·2018

Researchers synthesized a 22-residue peptide with a large lactam bridge. Solution cyclization yielded better results than solid-phase, though overall yields were comparable due to fewer purification steps in solid-phase synthesis.

Area of Science:

  • Peptide Chemistry
  • Organic Synthesis
  • Macromolecular Science

Background:

  • Solid-phase peptide synthesis (SPPS) is a cornerstone of peptide production.
  • Cyclization strategies are crucial for creating cyclic peptides with specific structures and functions.
  • Large lactam bridges present unique synthetic challenges due to conformational constraints.

Purpose of the Study:

  • To synthesize a 22-residue peptide incorporating a substantial sidechain lactam bridge (60-atom cycle).
  • To evaluate and compare different protecting group strategies for the synthesis of linear peptide precursors.
  • To investigate and optimize cyclization conditions, comparing solution-phase and solid-phase methods.

Main Methods:

  • Solid-phase peptide synthesis utilizing Fmoc/tBu/cyclohexyl, Fmoc/tBu/allyl, or Boc/Bzl/fluorenylmethyl protecting groups.

Related Experiment Videos

  • Linear precursor synthesis followed by cyclization in either solution or on solid support.
  • Purification and characterization of the synthesized cyclic peptide.

    • Main Results:

    • Successful synthesis of a 22-residue peptide with an 18-residue sidechain lactam bridge.
    • Solution-phase cyclization consistently provided higher yields compared to solid-phase cyclization.
    • The solid-phase cyclization strategy, despite lower yields, necessitated fewer purification steps, leading to comparable overall yields.

    Conclusions:

    • Both solution and solid-phase cyclization methods are viable for synthesizing large cyclic peptides.
    • The choice between solution and solid-phase cyclization depends on balancing cyclization efficiency with purification requirements.
    • Protecting group selection significantly influences the success of linear precursor synthesis and subsequent cyclization.