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. 2021 Jun 3;86(13):9225–9232. doi: 10.1021/acs.joc.1c00853

Table 2. Solid-Phase Synthesis of Gly-Ψ[CH(CF3)NH]-Peptides.

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entry FmocNH-Gly-Ψ[CH(CF3)NH]-dipeptide peptide sequence purity (%)e mass, mg (yield, %) calculated mass observed mass
1 4ca H2N-Tyr-GlyΨ[CH(CF3)NH]-Phe-Ala-OH, 6c 96 9.4 (34) 510.51 511.2 [M + H]+
2 4ib H2N-Tyr-GlyΨ[CH(CF3)NH]-Asp-Ala-OH, 7c 97 10.3 (38) 478.17 479.2 [M + H]+
3 4jb H2N-Tyr-GlyΨ[CH(CF3)NH]-Lys-Ala-OH, 8c 95 8.4 (32) 491.51 492.2 [M + H]+
4 4hb H2N-Tyr-GlyΨ[CH(CF3)NH]-Arg-Ala-OH, 9c 96 20.3 (45) 519.53 520.3 [M + H]+
5 4ca H2N-Tyr-Gly-GlyΨ[CH(CF3)NH]-Phe-Leu-OH, 10d 96 15.3 (28) 609.65 610.4 [M + H]+
6 4jb Ac-Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-GlyΨ[CH(CF3)NH]-Lys-Pro-Val-CONH2, 11d 95f 19.9 (25) 1719.82 859.9 [M + H]2+
a

Treated with 30% TFA in DCM to form the free carboxylic acid from the precursor tert-Bu ester.

b

Treated with 2% TFA in DCM to form the free carboxylic acid from the precursor cumyl ester.

c

Synthesis performed manually in a single vial.

d

Synthesis performed in an automated synthesizer.

e

Determined by reverse phase HPLC.

f

Improved to >98% after a second purification.