Fmoc-L-Sez-OH

Chemical name: Fmoc selenazolidine carboxylic acid // Synonyms: 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-carboxylicacid

  • Product code:FAA8860
  • CAS No.:1985651-74-8
  • Formula:C19H17NO4Se
  • Molecular weight:402.31 g/mol
  • Purity :min.98%
  • Enantiomeric Purity:min.99,9%

Starting at $260.00

Grouped product items
Qty Packing unit Price SKU
250 mg
$260.00
FAA8860.0250
500 mg
$468.00
FAA8860.0500
1 g
$728.00
FAA8860.1000
5 g
$2,600.00
FAA8860.5000
Safety Data Sheets
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-γ; 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


Bulk or large quantity order?

Do you need larger quantities for your development or production?

Do you need further information about this product?

get in contact

Quick contact

Please send me more information about

We found other products you might like!