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(Boc-L-Sec)2
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
- Molecular weight:534.35 g/mol
- Purity :min. 97%
- Enantiomeric Purity:min. 99,7%
from $131.25
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 α-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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