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

Solid-phase synthesis and structural characterization of highly substituted hydroxyproline-based

Bianco1, Sonksen, Roepstorff

  • 1Laboratoire de Chimie Immunologique, UPR 9021 CNRS, Institut de Biologie Moleculaire et Cellulaire, Strasbourg, France.

The Journal of Organic Chemistry
|April 25, 2000
PubMed
Summary

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

Can one lung ventilation prevent air embolism in the lung injury victim?

Current surgery·2000
Same author

Partial characterization and localization of a novel type of antifungal protein (IWF6) isolated from sugar beet leaves.

Plant science : an international journal of experimental plant biology·2000
Same author

Conformational study by CD of chirally tethered naphthalene moieties: toward an understanding of the asymmetric intramolecular coupling reaction?

Chirality·2000
Same author

Characterization of a new antifungal non-specific lipid transfer protein (nsLTP) from sugar beet leaves.

Plant science : an international journal of experimental plant biology·2000
Same author

Stereoselective alkylation of N-Boc-protected-5-substituted delta-lactams: synthesis of alpha, delta-disubstituted delta-amino acids

Organic letters·2000
Same author

Characterization of specificity of subtilisin Carlsberg towards peptide T by high-performance liquid chromatography and electrospray mass spectrometry.

Enzyme and microbial technology·2000

New solid-phase methods enable synthesis of diverse 2,5-diketopiperazines (DKPs) using hydroxyproline. These heterocyclic molecules show potential as enzyme inhibitors.

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Chemistry

Background:

  • 2,5-diketopiperazines (DKPs) are privileged heterocyclic scaffolds.
  • Incorporating trans-4-hydroxy-L-proline (Hyp) offers unique structural features.
  • Novel synthetic routes are needed to access diverse DKP libraries.

Purpose of the Study:

  • To develop general solid-phase synthesis methods for novel DKPs.
  • To introduce molecular diversity at multiple positions of the DKP scaffold.
  • To explore the application of these DKPs as potential enzyme inhibitors.

Main Methods:

  • Solid-phase synthesis utilizing Ellman resin.
  • N-protection and methyl esterification of hydroxyproline.
  • Sequential reactions including Hyp alkylation, N-acylation, cyclization, and amide bond alkylation.

Related Experiment Videos

Main Results:

  • Successful synthesis of highly functionalized bicyclic DKPs.
  • Introduction of up to three centers of molecular diversity.
  • Observation of epimerization during backbone amide bond alkylation.
  • Elucidation of DKP structures using multidimensional NMR.

Conclusions:

  • Developed versatile solid-phase strategies for DKP synthesis.
  • Demonstrated the potential for generating diverse heterocyclic compounds.
  • Highlighted the applicability of these methods for discovering enzyme inhibitors.