Methyl to trifluoromethyl substitution as a strategy to increase the membrane permeability of short peptides. Issue 43 (22nd October 2021)

• Record Type: Journal Article
• Authors: Ono, Takahiro; Aikawa, Kohsuke; Okazoe, Takashi; Morimoto, Jumpei; Sando, Shinsuke
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 43(2021)
• Page Start: 9386
• Page End: 9389
• Publication Date: 2021-10-22
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01565f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : CH3 to CF3 substitution on a side chain of proteiogenic amino acids increases the membrane permeability of peptides. Abstract : Here, we investigated the effect of CH3 to CF3 substitution on the membrane permeability of peptides. We synthesized a series of peptides with CF3 groups and corresponding nonfluorinated peptides and measured the membrane permeability of the peptides. As a result, we demonstrated that CH3 to CF3 substitution is useful for increasing the membrane permeability of di-/tri-peptides.