Fmoc-Sez

References

This selenocysteine-derived building-block is used in NCL/deselenization technique. NCL is performed at selenocysteine followed by a selective deselenization reaction,
which converts the Sec at the ligation site into Ala in the presence of unprotected Cys residues.

Sez is deprotected into Sec by treatment with MeONH₂ at pH 4.

The deselenization reaction is done using TCEP in the presence of DTT.

Org. Biomol. Chem., 2016,14, 8101-8108;

Angew. Chem. Int. Ed. 2016, 55, 992 –995;

https://doi.org/10.1002/anie.201509378

Org. Lett. 2020, 22, 17, 6863–6867;

https://doi.org/10.1021/acs.orglett.0c02401

Sez can also be deprotected using Cu(II) salts:

J. Org. Chem. 2020, 85, 3, 1425–1433;

https://doi.org/10.1021/acs.joc.9b02388

J. Org. Chem. 2020, 85, 3, 1731–1739;

https://doi.org/10.1021/acs.joc.9b02644

Fmoc-deprotection and Sez-opening can be done in one pot.

Chem.-Eur. J., 2022, 28, 16, e202200279