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- W2048521567 abstract "Abstract: The proximity of the α ‐amine and β ‐thiol of α ‐amino terminal‐cysteine (NT‐Cys) residues in peptides imparts unique chemical properties that have been exploited for inter‐ and intra‐molecular ligation of unprotected peptides obtained through both synthetic and biological means. A reversible protecting group orthogonal to other protection strategies and reversible under mild conditions would be useful in simplifying the synthesis, cleavage, purification and handling of such NT‐Cys peptides. It could also be useful for the sequential ligation of peptides. To this end, we explored tri‐one chemistry and found that ninhydrin (indane‐1,2,3 trione) reacted readily with cysteine or an NT‐Cys‐containing peptide on‐ or off‐resin at pH 2–5 to form Ninhydrin‐protected Cys (Nin‐Cys) as a thiazolidine (Thz). The Thz ring, protecting both the amino and thiol groups in Nin‐Cys, completely avoids the formylation and Thz side reactions found during hydrofluoric acid (HF) cleavage when N‐ π ‐benzyloxymethyl histidine groups are present. Nin‐Cys is stable during coupling reactions and various cleavage conditions with trifluoroacetic acid or HF, but is deprotected under thiolytic or reducing conditions. These properties enable a facile one‐step deprotection and end‐to‐end‐cyclization reaction of Nin‐Cys peptides containing C‐terminal thioesters." @default.
- W2048521567 created "2016-06-24" @default.
- W2048521567 creator A5011537784 @default.
- W2048521567 creator A5065310417 @default.
- W2048521567 creator A5065442137 @default.
- W2048521567 date "2004-03-01" @default.
- W2048521567 modified "2023-10-16" @default.
- W2048521567 title "Ninhydrin as a reversible protecting group of amino-terminal cysteine" @default.
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- W2048521567 doi "https://doi.org/10.1111/j.1399-3011.2004.00127.x" @default.
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