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. Author manuscript; available in PMC: 2014 Oct 27.
Published in final edited form as: J Am Chem Soc. 2013 Mar 11;135(11):4333–4363. doi: 10.1021/ja3109664

Scheme 20.

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.