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Fmoc-L-Sec(Mob)-OH
Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-Se-(4-methoxybenzyl)-L-selenocysteine // Synonyms: Fmoc-L-Sec(pMeOBzl)-OH, Fmoc-L-Sec(Pmb)-OH, Fmoc-Sec(Mob), Fmoc-L-4-methoxybenzyl selenocysteine,(2R)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-[4-methoxybenzyl)selanyl]propionic acid, Fmoc-Sec( MPM), (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)a
- Product code:FAA8705
- CAS No.:150308-80-8
- Formula:C26H25NO5Se
- Molecular weight:510.46 g/mol
- Purity :min. 99%
- Enantiomeric Purity:min. 99,9%
from $112.50
description
Building block for the introduction of selenocysteine by SPPS. Peptides containing selenocysteine can be cleaved from the resin with simultaneous side-chain deprotection by treatment with 5% (v/v) water, 95% (v/v) trifluoroacetic acid (TFA), 0.4 M 2,2’-dithiobis(5-nitropyridine) (DTNP) for 7 min at 60 °C or 2 h at RT. See also FAA8710 Fmoc-D-Sec(Mob)-OH.
references
A chemoselective strategy for late-stage functionalization of complex small molecules with polypeptides and proteins; D. T. Cohen, C. Zhang, C. M. Fadzen, A. J. Mijalis, L. Hie, K. D. Johnson, Z. Shriver, O. Plante, S. J. Miller, S. L. Buchwald, B. L. Pentelute;
Nat. Chem. 2019; 11: 78-85. https://doi.org/10.1038/s41557-018-0154-0.
Chemical synthesis of ferredoxin with 4 selenocysteine residues using a segment condensation method; T. Takei, T. Ando, T. Takao, Y. Ohnishi, G. Kurisu, M. Iwaoka, H. Hojo; Chem. Commun. 2020; 56: 14239-14242; https://doi.org/10.1039/D0CC06252A.
Reassessment of an Innovative Insulin Analogue Excludes Protracted Action yet Highlights the Distinction between External and Internal Diselenide Bridges; B. Dhayalan, Y.-S. Chen, N. B. Phillips, M. Swain, N. K. Rege, A. Mirsalehi, M. Jarosinski, F. Ismail-Beigi, N. Metanis, M. A. Weiss; Chem. Eur. J. 2020; 26(21): 4695-4700. https://doi.org/10.1002/chem.202000309.
Copper-Mediated Selenazolidine Deprotection Enables One-Pot Chemical Synthesis of Challenging Proteins; Z. Zhao, N. Metanis; Angew. Chem. Int. Ed. 2019; 58(41): 14610-14614. https://doi.org/10.1002/anie.201909484.
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