A new Oxyma derivative for nonracemizable amide-forming reactions in water.
An Oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate (2), displayed remarkable physicochemical properties as a peptide-coupling additive for peptide-forming reactions in water. Short peptides to oligopeptides could be synthesized by using 2, EDCI, and NaHCO(3) in water without measurable racemization. Significantly, a simple basic and acidic aqueous workup procedure can remove all reagents utilized in the reactions to afford only coupling products in consistently excellent yields.
Department of Pharmaceutical Sciences, College of Pharmacy, University of Tennessee Health Science Center, 881 Madison, Memphis, Tennessee 38163-0001, USA.
Qinghui
Q
Wang
Yong
Y
Wang
Michio
M
Kurosu
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011245:Pregnadienes / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
D000577:Amides; D011245:Pregnadienes; D014867:Water; C045419:oxyma