(Boc-L-Sec)2

Gefahrgut

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

Art-Nr.:BAA3680
CAS Nr.:877754-71-7
Formel:C₁₆H₂₈N₂O₈Se₂
Lagertemperatur:-20°C
Molare Masse:534,35 g/mol
Reinheit:min. 97%
Enantiomerenreinheit:min. 99,7%

Ab 105,00 €

Gruppiert Produkte - Artikel
Anzahl	Verpackungsgröße	Preis	SKU	Warenverfügbarkeit
	100 mg	105,00 €	BAA3680.0100	<10 Arbeitstage
	250 mg	175,00 €	BAA3680.0250	<10 Arbeitstage
	500 mg	315,00 €	BAA3680.0500	<10 Arbeitstage
	1 g	490,00 €	BAA3680.1000	<10 Arbeitstage
	5 g	1.750,00 €	BAA3680.5000	<10 Arbeitstage
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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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