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tBu-SS-Photo(Fmoc)-Gly-OH
Nom chimique: Photocleavable-NCL-auxiliary-Gly-OH // Synonymes: 2-(1-(4-(4-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)ethylamino)-4-oxobutoxy)-5-methoxy-2-nitrophenyl)-2-(tert-butyldisulfanyl)ethylamino)acetic acid
- n° Art.:PAA2000
- n° CAS:1994388-93-0
- Formule:C36H44N4O9S2
- Masse moléculaire:740,89 g/mol
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description
New auxiliary reagent for native chemical ligation (NCL) at the position of glycine in a peptide sequence. After coupling of this building block at the N-terminus of a peptide the Fmoc protecting group can be removed under standard conditions and acylated with mPEG-carboxylic acids, in order to improve the solubility of the resulting deprotected peptide. After cleavage from the resin t-butylmercaptane is being removed under reductive conditions with TCEP. The resulting free peptide thiol undergoes acylation with peptide thioesters, followed by an S to N acyl shift resulting the corresponding peptide bond. The auxiliary group can easily be removed with UV light (10 min in water or water/acetonitrile). This method is particularly useful for the synthesis of sophisticated peptides, like glycopeptides, where cost sand labor intensive, short sequences can be prepared separately and conjugated with long fragments, which can be synthesized in a standard manner.
references
Ein PEGyliertes, lichtspaltbares Auxiliar für die sequenzielle enzymatische Glykosylierung und native chemische Ligation von Peptiden; Claudia Bello, Shuo Wang, Lu Meng, Kelly W. Moremen, Christian Becker; Angew. Chem. 2015; 127: 7823-7828; DOI: 10.1002/ange.201501517.
A PEGylated Photocleavable Auxiliary Mediates the Sequential Enzymatic Glycosylation and Native Chemical Ligation of Peptides; Claudia Bello, Shuo Wang, Lu Meng, Kelly W. Moremen, Christian Becker; Angew. Chem. Int. Ed. 2015; 54: 7711-7715; DOI: 10.1002/anie.201501517.
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