Scheme 20.
Oxime reactions in aqueous solution. Right: HPLC chromatograms of reactions. For each, top panel: starting material used for that reaction, bottom panel: crude HPLC of reaction products. The reaction with oxoproline to synthesize 123 generates two products that were indistinguishable by NMR and mass spectrometry, presumably the E and Z oximes. RN = Ac-Thr-Tyr-, RC = -Asn-NH2.