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. 2023 May;29(5):e3464.
doi: 10.1002/psc.3464. Epub 2022 Dec 19.

Chemical synthesis of per-selenocysteine human epidermal growth factor

Toshiki Takei  1 , Hideaki Tanaka  1 , Nobuaki Okumura  1 , Toshifumi Takao  1 , Luis Moroder  2 , Hironobu Hojo  1
Affiliations

Chemical synthesis of per-selenocysteine human epidermal growth factor

Toshiki Takei et al. J Pept Sci. 2023 May.

Abstract

Human seleno-epidermal growth factor (seleno-EGF), a 53-residue peptide where all six cysteine residues of the parent human EGF sequence were replaced by selenocysteines, was synthesized and the oxidative folding of a polypeptide containing three diselenide bonds was compared to that of the parent cysteine peptide. The crude high performance liquid chromatography (HPLC) profiles clearly showed that both the native EGF and its selenocysteine-analogue fold smoothly, yielding a single sharp peak, proving that even in the case of three disulfide-bonded polypeptides the disulfide-to-diselenide bond substitution is highly isomorphous, as confirmed by conformational circular dichroism measurements and particularly by the biological assays.

Keywords: Cys-to-Sec substitution; enhanced stability to reduction; epidermal growth factor; oxidative folding; selenocysteine.

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References

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