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. Author manuscript; available in PMC: 2018 Apr 10.
Published in final edited form as: J Am Chem Soc. 2016 Oct 17;138(42):13774–13777. doi: 10.1021/jacs.6b05688

Scheme 3.

Scheme 3

Synthesis of Ub-Dha-TRIM-25 (9)a

a(i) (1) 5% H2N–NH2 in DMF; (2) 6, DIC/Oxyma, 13%. (ii) (1) 5 M Gn-HCl, 1.6 M MeONH2, pH 5, 80%; (2) 2, 5% DMF, 6 M Gn-HCl, 100 mM MPAA, 100 mM NaPi, 1 mM EDTA, pH 7.5, 43%. (iii) 28 mM α,α′-dibromoadipoylbis(amide), pH 3.4, 0 °C, 12 h, 27%.