(Boc-L-Sec)2

Hazmat

Chemical name: N-alpha-t-Butyloxycarbonyl-L-selenocystine // Synonyms: Boc-L-Selenocystine, Boc-Selenocystine, (Boc-Sec-OH)2, (2R,2'R)-3,3'-diselanediylbis(2-(t-butoxycarbonylamino)propanoic acid), (Boc-Sec)2

Product code:BAA3680
CAS No.:877754-71-7
Formula:C₁₆H₂₈N₂O₈Se₂
Storage temperature:-20°C
Molecular weight:534.35 g/mol
Purity :min. 97%
Enantiomeric Purity:min. 99.7%

from €105.00

Grouped product items
Qty	Packing unit	Price	SKU	Availability
	100 mg	€105.00	BAA3680.0100	<10 business days
	250 mg	€175.00	BAA3680.0250	<10 business days
	500 mg	€315.00	BAA3680.0500	<10 business days
	1 g	€490.00	BAA3680.1000	<10 business days
	5 g	€1,750.00	BAA3680.5000	<10 business days
Safety Data Sheets

Skip to the end of the images gallery

Skip to the beginning of the images gallery

description

Selenocysteine (Sec) is a natural amino acid and this building block can be used to incorporate it into a peptide sequence. Sec has also been used successfully for native chemical ligation (NCL), as selenium shows higher nucleophilicity than sulfur. Acylation with an amino acid will result in a selenium ester as intermediate. After Se-to-N acyl shift the thermodynamically more stable amid will result forming a natural amide bond. Deselenification can be carried out with reductive agents yielding alanine at this position in the peptide sequence.

references

Selenopeptide chemistry; M. Muttenthaler, P. F. Alewood; J. Pept. Sci. 2008; 14(12): 1223-1239. https://doi.org/10.1002/psc.1075

Rapid Additive-Free Selenocystine−Selenoester Peptide Ligation; N. J. Mitchell, L. R. Malins, X. Liu, R. E. Thompson, B. Chan, L. Radom, R. J. Payne; J. Am. Chem. Soc. 2015; 137: 14011−14014. https://doi.org/10.1021/jacs.5b07237

Oxidative Deselenization of Selenocysteine: Applications for Programmed Ligation at Serine; L. R. Malins, N. J. Mitchell, S. McGowan, R. J. Payne; Angew. Chem. Int. Ed. 2015; 54: 12716 -12721. https://doi.org/10.1002/anie.201504639

Selenopeptide chemistry; Markus Muttenthaler, Paul F. Alewood; J. Pept. Sci. 2008; 14(12): 1223-1239. https://doi.org/10.1002/psc.1075

Synthesis of selenocysteine peptides and their oxidation to diselenide‐bridged compounds; D. Besse, L. Moroder; J. Peptide Sci. 1997; 3(6): 442-453. https://doi.org/10.1002/(SICI)1099-1387(199711)3:6<442::AID-PSC122>3.0.CO;2-2

Synthetic study on selenocystine containing peptides; T. Koide, H. Itoh, A. Otaka, H. Yasui, M. Kuroda, N. Esaki, K. Soda, N. Fujii; Chem. Pharm. Bull. 1993; 41(3): 502-506. https://doi.org/10.1248/cpb.41.502

Syntheses and Biological Activities of Selenium Analogs of á-Rat Atrial Natriuretic Peptide; T. Koide, H. Itoh, A. Otaka, M. Furuya, Y. Kitajima, N. Fujii; Chem. Pharm. Bull. 1993; 41(9): 1596-1600. https://doi.org/10.1248/cpb.41.1596

* Disclaimer

We refer to our general terms and conditions.
All information contained in our webshop is compiled to the best of our knowledge.
Prices and product availability are subject to change and require reconfirmation. Please contact us for further information.