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. 2013 Jul 8;11(7):2382–2397. doi: 10.3390/md11072382

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© 2013 by the authors; licensee MDPI, Basel, Switzerland.

This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).

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Scheme 2 — Fmoc-SPPS of resin bound intermediates 20–23. Reagents and conditions: (a) Deprotection: 10 vol% piperidine/DMF, 2 × 3 min Coupling: 5 eq Fmoc-Leu-OH or Fmoc-Val-OH, 5 equiv. HATU, 10 equiv. iPr₂EtN, 2 × 6 h; (b) (One cycle) Deprotection: 10 vol% piperidine/DMF, 2 × 3 min; Coupling 1 [Fmoc-Gln(Trt)-OH and Fmoc-Asn(Trt)-OH]: 4 eq AA, 4 eq PyBOP, 8 eq NMM, 1–2 h; or Coupling 2 (for fatty acid 5, 10, or 11): 1.2 eq acid, 1.2 eq HATU, 2.4 eq iPr₂EtN; and Capping: 10 vol% acetic anhydride/pyridine, 2 min; (c) TFA:TIS:H₂O, (9:0.5:0.5, v/v/v), 1 h; (d) LiAlH₄, THF, 0 °C, then KHSO₄, NaKTartrate, 0 °C to r.t.