226956-06-5Relevant academic research and scientific papers
Total synthesis of unguisin A
Hunter, Luke,Chung, Jonathan H.
, p. 5502 - 5505 (2011)
The first synthesis of the γ-aminobutyric acid (GABA)-containing cyclic heptapeptide unguisin A is reported, confirming the structure of this natural product. Macrocyclization of a flexible GABA-containing linear precursor is found to proceed rapidly and in good yield.
Stereoselective fluorination alters the geometry of a cyclic peptide: Exploration of backbone-fluorinated analogues of unguisin a
Hu, Xiang-Guo,Thomas, Donald S.,Griffith, Renate,Hunter, Luke
, p. 6176 - 6179 (2014)
New methods for enhancing the efficiency of peptide cyclization, and for fine-tuning the conformations of cyclic peptides, are valuable from a drug development perspective. Herein stereoselective fluorination is investigated as a new strategy for achieving these goals. Four vicinal difluorinated analogues of the natural cyclic heptapeptide unguisin A have been efficiently synthesized. The analogues are found to adopt dramatically different secondary structures, controlled by the fluorine stereochemistry.
