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Related Concept Videos

Translesion DNA Polymerases02:10

Translesion DNA Polymerases

Translesion (TLS) polymerases rescue stalled DNA polymerases at sites of damaged bases by replacing the replicative polymerase and installing a nucleotide across the damaged site. Doing so, TLS allows additional time for the cell to repair the damage before resuming regular DNA replication.
TLS polymerases are found in all three domains of life - archaea, bacteria, and eukaryotes. Of the different classes of TLS polymerases, members of the Y family are fitted with specialized structures that...

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Related Experiment Video

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Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
11:42

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology

Published on: May 15, 2012

An oxidatively-activated safety catch linker for solid phase synthesis.

Stephen G Davies1, Duncan A B Mortimer, Andrew W Mulvaney

  • 1Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK. steve.davies@chem.ox.ac.uk

Organic & Biomolecular Chemistry
|April 19, 2008
PubMed
Summary
This summary is machine-generated.

A novel safety catch linker system based on N-benzyl-4-amino-2,2-dimethylbutanoic acid enables reaction monitoring and optimization. This oxidatively activated system facilitates the release of alcohols and amines from solid supports during synthesis.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Solid-Phase Synthesis

Background:

  • Development of robust and versatile linker systems is crucial for solid-phase synthesis.
  • Existing methods often lack efficient monitoring or facile release mechanisms.
  • Safety catch linkers offer controlled cleavage under specific activation conditions.

Purpose of the Study:

  • To develop a new oxidatively activated safety catch linker for solid-phase synthesis.
  • To enable reaction monitoring and optimization during solid-phase reactions.
  • To demonstrate the linker's utility in synthesizing diverse compounds and handling chiral auxiliaries.

Main Methods:

  • Design and synthesis of an N-benzyl-4-amino-2,2-dimethylbutanoic acid-based linker.
  • Utilizing CAN (Ceric Ammonium Nitrate) for oxidative debenzylation and subsequent cyclization.
  • Application in solution-phase model studies and solid-phase synthesis.

Main Results:

  • Successful demonstration of CAN-promoted oxidative debenzylation of the tertiary N-benzylamine.
  • Concomitant cyclization and release of alcohols and amines were achieved.
  • The linker was effectively applied to solid-phase synthesis of phenol derivatives and chiral auxiliary manipulation.

Conclusions:

  • The developed linker system provides a reliable method for oxidative activation and cleavage on solid supports.
  • This system facilitates reaction monitoring and optimization in solid-phase synthesis.
  • It offers a versatile platform for the synthesis of complex molecules and the management of chiral auxiliaries.