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Boc-L-Sec(Mob)-OH
Chemical name: N-alpha-t-Butyloxycarbonyl-Se-(4-methoxybenzyl)-L-selenocysteine // Synonyms: Boc-Sec(PMB)-OH, Boc-Sec(pMeOBzl)-OH, (R)-2-(t-butoxycarbonylamino)-3-(4-methoxybenzylselanyl)propanoic acid, Boc-Sec(Mob)-OH
- Product code:BAA3760
- CAS No.:959415-39-5
- Formula:C16H23NO5Se
- Storage temperature:2-8°C
- Molecular weight:388.32 g/mol
- Purity :min. 98%
- Enantiomeric Purity:min. 99,9%
from €108.00
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 SeàN 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; Markus Muttenthaler, Paul F. Alewood; J. Pept. Sci. 2008; 14(12): 1223-1239. DOI: org/10.1002/psc.1075
Rapid Additive-Free Selenocystine−Selenoester Peptide Ligation; Nicholas J. Mitchell, Lara R. Malins, Xuyu Liu, Robert E. Thompson, Bun Chan, Leo Radom, and Richard J. Payne; J. Am. Chem. Soc. 2015; 137: 14011−14014. DOI: 10.1021/jacs.5b07237
Oxidative Deselenization of Selenocysteine: Applications for Programmed Ligation at Serine; Lara R. Malins, Nicholas J. Mitchell, Sheena McGowan, and Richard J. Payne; Angew. Chem. Int. Ed. 2015; 54: 12716 -12721. DOI: 10.1002/anie.201504639
Selenopeptide chemistry; Markus Muttenthaler, Paul F. Alewood; J. Pept. Sci. 2008; 14(12): 1223-1239. DOI: org/10.1002/psc.1075
Synthesis of selenocysteine peptides and their oxidation to diselenide‐bridged compounds; Dörthe Besse, Luis Moroder; J. Peptide Sci. 1997; 3(6): 442-453. DOI: org/10.1002/(SICI)1099-1387(199711)3:6<442::AID-PSC122>3.0.CO;2-2
Synthetic study on selenocystine containing peptides; Takaki Koide, Hiromi Itoh, Akira Otaka, , Hiroyuki Yasui, Masataka Kuroda, Nobuyoshi Esaki, Kenji Soda, Nobutaka Fujii; Chem. Pharm. Bull. 1993; 41(3): 502-506. DOI: org/10.1248/cpb.41.502
Syntheses and Biological Activities of Selenium Analogs of á-Rat Atrial Natriuretic Peptide; Takaki Koide, Hiromi Itoh, Akira Otaka, Mayumi Furuya, Yasuo Kitajima, Nobutaka Fujii; Chem. Pharm. Bull. 1993; 41(9): 1596-1600 . DOI: org/10.1248/cpb.41.1596
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