4.5 Article

Solid Phase Synthesis of Thioether-linked Peptide Macrocycles via Palladium-Catalyzed Intramolecular S-Arylation and S-Alkenylation

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue 11, Pages 2888-2891

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202100561

Keywords

solid phase synthesis; peptide macrocycles; S-arylation; bicyclic peptides; palladium catalysis

Funding

  1. 111 project of MOE China [B06005]
  2. [NSFC-21725204]
  3. [NSFC-22071119]
  4. [NCC2020FH02]

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A new protocol for the synthesis of thioether-linked peptide macrocycles has been developed, using PEGA resin and a mixed solvent of CH3CN and H2O. This method allows for the preparation of peptide macrocycles of varied ring size, composition, and with different thioether linkers in moderate to good yield with one column chromatography purification.
A new protocol for synthesis of thioether-linked peptide macrocycles via Pd-catalyzed intramolecular S-arylation and S-alkenylation on solid phase is developed. The use of PEGA resin in mixed solvents of CH3CN and H2O is critical to suppress the undesired S-arylation reactions with the XantPhos-Pd-G3 catalyst. Peptide macrocycles of varied ring size, composition, and with different thioether linkers can be prepared in moderate to good yield with one column chromatography purification.

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