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. 2017 Sep 7;139(37):13063–13075. doi: 10.1021/jacs.7b06506

Scheme 1. Synthesis of Lanthionine-Bridged Peptide 2a.

Scheme 1

Reagents and conditions: (i) (allyl, Aloc/Fmoc)-lanthionine 1, PyAOP, HOAt, DIPEA, DMF, μwave, 5 min, 60 °C; (ii) incorporation of standard protected amino acids with HBTU, DIPEA, DMF, followed by deprotection with piperidine; (iii) Pd(PPh3)4, 1,3-dimethylbarbituric acid, DMF, CH2Cl2, then 40% piperidine/DMF; (iv) PyAOP, HOAt, DIPEA, DMF, μwave, 5 min, 60 °C; (v) Fmoc-Lys(Boc)-OH, HBTU, DIPEA, DMF, then 20% piperidine/DMF; (vi) TFA, ethanedithiol, iPr3SiH, H2O.