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. Author manuscript; available in PMC: 2022 Sep 24.
Published in final edited form as: Org Biomol Chem. 2020 Sep 30;18(37):7253–7272. doi: 10.1039/d0ob01417f

Table 10.

Solution-phase, nucleophilic displacement of NAU-appended peptides to access unprotected C-terminally modified peptides.

graphic file with name nihms-1628130-t0032.jpg

entry Nuc-H base (equiv) solvent ratio of
97 98 99
1 BuNH2 - MeCN/H20 93 - 7
2 BuNH2 - MeCN >99 - -
3 aniline Hünig’s base (5) MeCN 8 92 -
4 MeOH Hünig’s base (5) MeCN 42 58 -
5 NaBH4 - THF/MeCN 77 - 23