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Proline editing alternative approach: automated synthesis of the peptide Ac-TYHypN-NH2(1) via TBS hydroxyl protection.a
a (a) 20% piperidine/DMF; (b) Fmoc-Asn(Trt)-OH, HBTU, DIPEA/DMF; (c) Fmoc-Tyr(OtBu)-OH, HBTU, DIPEA/DMF; (d) Fmoc-Thr(OtBu)-OH, HBTU, DIPEA/DMF; (e) 10% Ac2O/pyridine. RN′ = Ac-Thr(OtBu)-Tyr(OtBu)-, RC′ = -Asn(Trt)-NHRink-Resin. RN = Ac-Thr-Tyr-, RC = -Asn-NH2.
