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. 2023 Jul 10;16(7):985. doi: 10.3390/ph16070985

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© 2023 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 (CC BY) license (https://creativecommons.org/licenses/by/4.0/).

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Scheme 1 — Synthesis of DOTAM-TATE, eSOMA-01, and eSOMA-02: (i) Fmoc-Thr(tBu)-OH, DCM, DIPEA, 1 h 30 min, rt; (ii) DCM/MeOH/DIPEA (80:15:5 v/v/v), 15 min, rt; (iii) 20% 4-Methylpiperidine in DMF, 15 min, rt; (iv) Fmoc-Cys(Acm)-OH, HATU, DIPEA, 1 h, rt; (v) Elongation; (vi) Tl(TFA)₃, DMF, 1 h, rt; (vii) 4-(Fmoc-aminomethyl)cyclohexanecarboxylic acid (Fmoc-Amcha-OH) or Fmoc-4-amino-1-carboxymethyl-piperidine (Fmoc-Pip-OH), HATU, DIPEA, 1 h, rt; (viii) 20% 4-Methylpiperidine in DMF, 15 min, rt; (ix) DO3AM acetic acid, PyBop, DIPEA, overnight, rt; (x) TFA/H₂O/TIPS (95:2.5:25), 2 h, rt., 11% (DOTAM-TATE), 12% (eSOMA-01), and 7% (esOMA-02).