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Boc-L-Sez-OH
Chemical name: Boc selenazolidine carboxylic acid // Synonyms: Boc-Sez-OH, (4R)-3-[(tert-butoxy)carbonyl]-1,3-selenazolidine-4-carboxylic acid
- Product code:BAA4880
- CAS No.:1841180-44-6
- Storage temperature:2-8°C
- Formula:C9H15NO4Se
- Molecular weight:280.19 g/mol
- Purity :min.98%
from €108.00
description
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. Sez can also be deprotected using Cu(II) salts. The deselenization reaction is done using TCEP in the presence of DTT.
references
Chemical Synthesis of Proteins with Non-Strategically Placed Cysteines Using Selenazolidine and Selective Deselenization; P. S. Reddy, S. Dery, N. Metanis; Angew. Chem. Int. Ed. 2016; 55(3): 992-995. https://doi.org/10.1002/anie.201509378
Total Synthesis of Glycosylated Human Interferon-gamma; X. Wang, A. S. Ashhurst, L. J. Dowman, E. E. Watson, H. Y. Li, A. J. Fairbanks, M. Larance, A. Kwan, R. J. Payne; Org. Lett. 2020; 22(17): 6863-6867. https://doi.org/10.1021/acs.orglett.0c02401
Copper-Mediated Deprotection of Thiazolidine and Selenazolidine Derivatives Applied to Native Chemical Ligation; N. Naruse, D. Kobayashi, K. Ohkawachi, A. Shigenaga, A. Otaka; J. Org. Chem. 2020; 85(3): 1425-1433. https://doi.org/10.1021/acs.joc.9b02388
Utilizing Copper-Mediated Deprotection of Selenazolidine for Cyclic Peptide Synthesis; Z. Zhao, N. Metanis; J. Org. Chem. 2020; 85(3): 1731-1739. https://doi.org/10.1021/acs.joc.9b02644
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