Development of orthogonally protected hypusine for solid-phase peptide synthesis

The Journal of Organic Chemistry
Aimin SongKurt Deshayes

Abstract

An orthogonally protected hypusine reagent was developed for solid-phase synthesis of hypusinated peptides using the Fmoc/t-Bu protection strategy. The reagent was synthesized in an overall yield of 27% after seven steps from Cbz-Lys-OBzl and (R)-3-hydroxypyrrolidin-2-one. The side-chain protecting groups (Boc and t-Bu) are fully compatible with standard Fmoc chemistry and can be readily removed during the peptide cleavage step. The utility of the reagent was demonstrated by solid-phase synthesis of hypusinated peptides.

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Citations

Jan 19, 2016·Journal of Molecular Biology·Qianting ZhaiPaul J Carter
May 24, 2019·The Journal of Organic Chemistry·Robin J PrinceBrian T Hopkins

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