1277102-28-9Relevant academic research and scientific papers
Synthesis of difluorinated β- And γ-amino acids: Investigation of a challenging deoxyfluorination reaction
Wang, Zhiyong,Hunter, Luke
, p. 143 - 147,5 (2020/07/30)
Backbone-homologated amino acids containing the vicinal difluoride motif have been synthesised in a highly stereoselective manner. The key synthetic transformation is the DeoxoFluor-mediated fluorination of a vicinal fluorohydrin. The synthetic route is amenable to the production of all possible stereoisomers of α,β-difluoro-γ-aminobutyric acid. In addition, a novel difluoromethyl-substituted β-amino acid is accessed via an unexpected rearrangement process.
Synthesis and conformational analysis of α,β-difluoro-γ- amino acid derivatives
Hunter, Luke,Jolliffe, Katrina A.,Jordan, Meredith J. T.,Jensen, Paul,MacQuart, Rene B.
, p. 2340 - 2343 (2011/04/22)
Conformationally restricted amino acids are of interest because they can be incorporated into shape-controlled peptides for applications in biotechnology and medicine.Within this context, β-and γ-amino acids have attracted considerable attention since their homologated carbon backbones are amenable to functionalization in ways that are not achievable with a-amino acids. For example, Seebach et al. have shown that the different diastereoisomers of α-fluoroβ-alanine lead to differently folded structures when they are incorporated into b-heptapeptides. These conformational differences are attributed to the preference of C-F bonds to align antiparallel to adjacent amide C=O bonds and gauche to vicinal C-N bonds. This result is a notable example of a growing body of research demonstrating that the C-F bond can be exploited as a conformational tool to optimize the properties of diverse functional molecules including pharmaceuticals, organocatalysts and liquid crystals.
