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Boc-L-Cys(Phacm)-OH
Chemical name: N-alpha-t-Butyloxycarbonyl-S-(Phenylacetylaminomethyl)-L-cysteine
- Product code:BAA6390
- CAS No.:57084-73-8
- Formula:C17H24N2O5S
- Molecular weight:368.45 g/mol
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description
Enzyme-labile protecting groups have emerged as a green alternative to conventional protecting groups. These groups introduce a further orthogonal dimension and eco-friendliness into protection schemes for the synthesis of complex polyfunctional organic molecules. S-Phacm, a Cys-protecting group, can be easily removed by the action of a covalently immobilized PGA enzyme under very mild conditions.
references
Enzyme-Labile Protecting Groups for the Synthesis of Natural Products: Solid-Phase Synthesis of Thiocoraline; Judit Tulla-Puche, Miriam Gongora-Benitez, Nuria Bayo-Puxan, Andres M. Francesch, Carmen Cuevas, and Fernando Albericio;
Angew. Chem. Int. Ed. 2013; 52: 1-5. DOI: 10.1002/anie.201301708.
Eco-Friendly Combination of the Immobilized PGA Enzyme and the S-Phacm Protecting Group for the Synthesis of Cys-Containing Peptides; Miriam Góngora-Benítez, Alessandra Basso, Thomas Bruckdorfer, Miriam Royo, Judit Tulla-Puche, Fernando Albericio; Chemistry - A European Journal, Oct 2012; DOI: 10.1002/chem.201201370.
Additional References:
Hydrolysis of peptides by different enzymes; Siegmund Reissmann, Georg Greiner; Int. J. Peptide Protein Res. 1992; 40: 110-113. Zur Synthese symmetrischer und unsymmetrischer Cystinpeptide; H. Arnold, M. Eule in PEPTIDES 1972 Proceedings of the Twelfth European Peptide Symposium, Reinhardsbrunn Castle, German Democratic Republic, Horst Hanson, Hans-Dieter Jakubke (eds.), 1973; 78-85.
An Iodine-Free and Directed-Disulfide-Bond-Forming Route to Insulin Analogues; F. Liu, Q. Liu, A.R. Mezo; Org. Lett. 2014;
16: 3126?3129. DOI: dx.doi.org/10.1021/ol501252b.
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