(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 $131.25

Grouped product items
Qty	Packing unit	Price	SKU	Availability
	100 mg	$131.25	BAA3680.0100	<10 business days
	250 mg	$218.75	BAA3680.0250	<10 business days
	500 mg	$393.75	BAA3680.0500	<10 business days
	1 g	$612.50	BAA3680.1000	<10 business days
	5 g	$2,187.50	BAA3680.5000	<10 business days
Safety Data Sheets

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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

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