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. 2021 Jul 2;86(13):9225-9232.
doi: 10.1021/acs.joc.1c00853. Epub 2021 Jun 3.

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

Clara Sgorbati  1 , Eliana Lo Presti  2 , Greta Bergamaschi  2 , Monica Sani  2 , Alessandro Volonterio  1   2
Affiliations

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

Clara Sgorbati et al. J Org Chem. .

Abstract

The solid-phase synthesis of Gly-Ψ[CH(CF3)NH]-peptides is presented. In order to achieve this goal, the synthesis of Gly-Ψ[CH(CF3)NH]-dipeptides having the C-terminus unprotected, the N-terminus protected as Fmoc- or Teoc-, and possibly side chain functionalities protected with acid-labile protecting groups has been developed. A selected small library of six peptidomimetics, encompassing analogues of biological relevant peptides, have been obtained in high purity.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Ψ[CH(CF3)NH]-peptides and principal features of the trifluoroethylamine function.
Scheme 1
Scheme 1. Selective Ester Deprotection and Solution Phase Coupling
(i) 30% TFA, DCM, 12 h, rt; (ii) H-Phe-OMe, HBTU, DIPEA, DMF; (iii) H-Ile-OMe, HBTU, DIPEA, DMF; (iv) 1 M NaOH, THF, 24 h, rt; (v) 2% TFA, DCM, 1 h, rt.
See this image and copyright information in PMC

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