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. Author manuscript; available in PMC: 2020 Sep 23.
Published in final edited form as: Biochemistry. 2020 Aug 30;59(36):3300–3315. doi: 10.1021/acs.biochem.0c00608

Scheme 1: Synthetic route to obtain Cys-(αMe)Sec-Gly tripeptide.

Scheme 1:

(Top:) Starting with Boc-Cys(Mob)-OH, N,N′-dicyclohexylcarbodiimide (DCC) is used to make a symmetric anhydride intermediate in dichloromethane (DCM), which is then opened up using pentafluorophenol in ethyl acetate (EtOAc). The resulting Boc-Cys(Mob)-OPfP is added directly to the resin (grey sphere) with H-αMeSec(But)-Gly-OH dipeptide attached. SPPS procedures are used to perform ≥10 Boc-Cys(Mob)-OPfP couplings with N-methylmorpholine and no coupling reagents.