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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 1.

Scheme 1

Proline editing general approach: automated synthesis of the peptide Ac-TYHypN-NH2(1) via trityl 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. For all peptides in all schemes, the prime designation (e.g. 1′, RN′, RC′) indicates the protected peptide on solid phase, whereas the absence of a prime designation indicates free peptide in solution.