Boc-Sez

Synonyms
Boc-Sez-OH // (4R)‐3‐[(tert‐butoxy)carbonyl]‐1,3‐selenazolidine‐4‐carboxylic acid // Boc selenazolidine carboxylic acid // Boc-L-Sez-OH

ID

BO-167

Formula

C9H15NO4Se

CAS

1841180-44-6

MW

280.2

Purity

>98%

Storage

+2 to +8 °C

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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.

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

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