SCHEME 2.
Solid phase synthesis strategy to build JM79 homotrimers. The reagents and reaction conditions used are as follows: (1–2) a. Fmoc-Cys(Trt)-OH, HOBt, HBTU, DIPEA, b. 20% piperidine in DMF, c. Fmoc-Lys(ivDde)-OH, HOBt, HBTU, DIPEA. (2–3) a. 20% piperidine in DMF, b. Fmoc-Lys(Fmoc)-OH, HOBt, HBTU, DIPEA. (3–4) a. 5% hydrazine in DMF, v/v, b. 20% piperidine in DMF, c. Fmoc-β-Ala-OH (n = 6 Fmoc-AEEAc-OH addition), HOBt, HBTU, DIPEA. (4–5) a. 20% piperidine in DMF, b. addition of peptide portion (standard SPPS protocol to add Met, D-Lys, Lys). (5–6) a. 20% piperidine in DMF, b. addition of 5-mer peptoid portion (standard microwave-assisted peptoid synthesis). (6–7) 95% TFA, 2.5% TIS, 2.5% H2O (final product shown with AEEAc-OH).