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Disulfide-Based Protecting Groups for the Cysteine Side Chain.

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Two new disulfide-based protecting groups (SIT and MOT) are proposed for Cys thiol in the substitution of StBu, which is often difficult to remove. Both groups are based on a… Click to show full abstract

Two new disulfide-based protecting groups (SIT and MOT) are proposed for Cys thiol in the substitution of StBu, which is often difficult to remove. Both groups are based on a secondary thiol with a branched point in the β-position for an efficient modulation of its lability and/or stability. This unique structure allows them to be fully compatible with Fmoc/tBu SPPS. At the end of the synthesis, these groups are removed in a straightforward manner with dithiothreitol with some H2O.

Keywords: disulfide based; groups cysteine; side chain; protecting groups; cysteine side; based protecting

Journal Title: Organic letters
Year Published: 2020

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