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Fmoc-D-Lys(Ns)-OH
Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-epsilon-nosyl-D-lysine // Synonyms: N-alpha-Fmoc-N-epsilon-nosyl-D-lysine, N-alpha-Fmoc-N-epsilon-(2-nitrobenzenesulfonyl)-D-lysine,(R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(2-nitrophenylsulfonamido)hexanoic acid
- Product code:FAA4210
- CAS No.:2250437-39-7
- Formula:C27H27N3O8S
- Molecular weight:553.58 g/mol
- Purity :min. 98%
- Enantiomeric Purity:min. 99,7%
Starting at $149.50
description
Building block with side protection orthogonal to Fmoc/tBu strategy. Can be used for side specific derivatization, for example for TFA mediated in situ cyclization, which is taking advantage of intermediate aspartamide formation.
references
A Tandem In Situ Peptide Cyclization through Trifluoroacetic Acid Cleavage; Koushik Chandra, Tapta Kanchan Roy, Deborah E. Shalev, Abraham Loyter, Chaim Gilon, R. Benny Gerber, and Assaf Friedler; Angew. Chem. Int. Ed. 2014; 53: 9450-9455. DOI: 10.1002/anie.201402789.
Luca Monfregola, Marilisa Leone, Enrica Calce, Stefania De Luca; Postsynthetic Modification of Peptides via Chemoselective N-Alkylation of Their Side Chains; Org. Lett. 2012; 14(7): 1664-1667; doi 10.1021/ol300437w.
Stefania De Luca, Raffaella Della Moglie, Antonia De Capua, Giancarlo Morelli; New synthetic strategy for o-NBS protected amino acids and their use in synthesis of mono-benzylated peptides; Tetrahedron Lett. 2005; 46: 6637-6640; doi:10.1016/j.tetlet.2005.07.154.
Luca Monfregola, Stefania De Luca; Synthetic strategy for side chain mono-N-alkylation of Fmoc-amino acids promoted by molecular sieves; Amino Acids 2001; 41(4): 981-990; doi 10.1007/s00726-010-0798-6.
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