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Fmoc-L-Sez-OH
Chemischer Name: Fmoc selenazolidine carboxylic acid // Synonyme: Fmoc-Sez, Fmoc-Sez-OH, (4R)-3-{[(9H-fluoren-9-yl)methoxy]carbonyl}-1,3-selenazolidine-4-carboxylic acid, (R)-3-(((9H-fluoren-9-yl)methoxy)carbonyl)-1,3-selenazolidine-4-carboxylic acid
- Art-Nr.:FAA8860
- CAS Nr.:1985651-74-8
- Lagertemperatur:2-8°C
- Formel:C19H17NO4Se
- Molare Masse:402,31 g/mol
- Reinheit:min.98%
- Enantiomerenreinheit:min.99,9%
Ab 200,00 €
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. The deselenization reaction is done using TCEP in the presence of DTT. Sez can also be deprotected using Cu(II) salts. Fmoc-deprotection and Sez-opening can be done in one pot.
references
Selenazolidine: a selenium containing proline surrogate in peptide science; E. Cordeau, S. Cantel, D. Gagne, A. Lebrun, J. Martinez, G. Subra, C. Enjalbal; Org. Biomol. Chem. 2016(14): 8101-8108. https://doi.org/10.1039/C6OB01450J
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): 992 –995. https://doi.org/10.1002/anie.201509378
Total Synthesis of Glycosylated Human Interferon-ã; 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. Zao, N. Metanis; J. Org. Chem. 2020, 85(3): 1731–1739. https://doi.org/10.1021/acs.joc.9b02644
One-Pot Chemical Protein Synthesis Utilizing Fmoc-Masked Selenazolidine to Address the Redox Functionality of Human Selenoprotein; F. Z. Zhao, R. Mousa, N. Metanis; Chem.-Eur. J. 2022, 28(16): e202200279. https://doi.org/10.1002/chem.202200279
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