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. 2017 Oct 5;8(12):8183–8192. doi: 10.1039/c7sc03241b

Fig. 3. Synthesis of Leu10-teixobactin starting from 2-chlorotritylchloride resin: (a) 4 eq. Fmoc-Ala-OH/8 eq. DIPEA in DCM, 3 h. (b) 20% piperidine in DMF followed by 3 eq. AllocHN-d-Thr-OH, 3 eq. HATU/6 eq. DIPEA, 1.5 h. (c) 10 eq. Fmoc-Ile-OH, 10 eq. DIC, 5 mol% DMAP in DCM, 2 h followed by capping with Ac2O/DIPEA 10% in DMF, 20% piperidine in DMF. (d) 4 eq. Fmoc-Leu-OH, 4 eq. HATU/8 eq. DIPEA in DMF, 1 h followed by 20% piperidine in DMF. (e) 10 eq. Trt-Cl, 15% Et3N in DCM, 1 h. (f) 0.2 eq. [Pd(PPh3)4]0 + 24 eq. PhSiH3 in dry DCM, 1 × 20 min, 1 × 45 min. (g) 4 eq. Fmoc/Boc-AA(PG)-OH (AA = amino acid, PG = protecting group), 4 eq. DIC/Oxyma (μwave, 10 min) followed by 20% piperidine in DMF (3 min, 10 min). (h) TFA : TIS : DCM = 2 : 5 : 93, 1 h. (i) 1 eq. HATU/10 eq. DIPEA in DMF, 30 min. (j) TFA : TIS : H2O = 95 : 2.5 : 2.5, 1 h.

Fig. 3