Synthesis and Biological Evaluation of Gramicidin S??Inspired Cyclic Mixed α/β??Peptides

…, F Basalan, HC van de Mei, HJ Busscher…

Index: Van Der Knaap, Matthijs; Basalan, Fatih; Van De Mei, Henny C.; Busscher, Henk J.; Van Der Marel, Gijsbert A.; Overkleeft, Herman S.; Overhand, Mark Chemistry and Biodiversity, 2012 , vol. 9, # 11 p. 2494 - 2506

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Citation Number: 3

Abstract

Abstract Via a Mannich reaction involving a dibenzyliminium species and the titanium enolates of Evans' chiral acylated oxazolidinones the β 2-amino acids (R)-and (S)-Fmoc-β 2 homovaline and (R)-Fmoc-β 2 homoleucine are synthesized. These building blocks were used, in combination with commercially available α-and β 3-amino acids, for the synthesis of the cyclo-(αβ 3 αβ 2 α) 2 peptide 2 and the cyclo-(αβ 2 αβ 3 α) 2 peptides 3–5. The ...