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Boc-L-Phe(4-NH-Poc)-OH
Chemical name: N-alpha-t-Butyloxycarbonyl-4-(propargyloxycarbonyl)amino-L-phenylalanine // Synonyms: Boc-Phe(4-NH-Poc), Boc-L-Aph(Poc)-OH, Boc-4Aph(Poc), Boc-L-4Aph(Poc)-OH, Boc-L-4-Aph(Poc)-OH, Boc-p-amino-Phe(Poc)-OH, Boc-L-Phe(4-NH-Poc)-OH, Boc-4Aph(Pryoc),Boc-L-4Aph(Pryoc)-OH, Boc-L-4-Aph(Pryoc )-OH, Boc-p-amino-Phe(Pryoc)-OH, (2S)-2-{[(tert-bu
- Product code:BAA3980
- CAS No.:2576508-03-5
- Formula:C18H22N2O6
- Storage temperature:2-8°C
- Molecular weight:362.38 g/mol
- Purity :min. 99%
- Enantiomeric Purity:min. 99.7%
from €126.00
description
Used as an orthogonally protected building block in peptide synthesis. Propargyloxycarbonyl, commonly abbreviated as Poc or Pryoc, can either be used as alkyne component for standard Click conjugation or in combination with tetrazine linkers in copper-free Diels-Alder type Click reactions. It also has applications as unusual protecting group for amines, hydroxy functions and as esters. All 3 are stable to neat TFA, but can be cleaved at ambient temperature with Co2(CO)8 in TFA:DCM. Deprotection with other transition metals like palladium have also been reported.
references
Bioorthogonal Catalysis: A General Method To Evaluate Metal-Catalyzed Reactions in Real Time in Living Systems Using a Cellular Luciferase Reporter System; H. T. Hsu, B. M. Trantow, R. M. Waymouth and P. A. Wender; Bioconjug Chem 2016; 27: 376-82. https://doi.org/10.1021/acs.bioconjchem.5b00469
N-alkynyl derivatives of 5-fluorouracil: susceptibility to palladium-mediated dealkylation and toxigenicity in cancer cell culture; J. T. Weiss, C. Fraser, B. Rubio-Ruiz, S. H. Myers, R. Crispin, J. C. Dawson, V. G. Brunton, E. E. Patton, N. O. Carragher and A. Unciti-Broceta; Front Chem 2014; 2: 56. https://doi.org/10.3389/fchem.2014.00056
Palladium-triggered deprotection chemistry for protein activation in living cells; J. Li, J. Yu, J. Zhao, J. Wang, S. Zheng, S. Lin, L. Chen, M. Yang, S. Jia, X. Zhang and P. R. Chen; Nat Chem 2014; 6: 352-61. https://doi.org/10.1038/nchem.1887
Propargyloxycarbonyl and propargyl groups for novel protection of amino, hydroxy, and carboxy functions; Y. Fukase, K. Fukase and S. Kusumoto; Tetrahedron Letters 1999; 40: 1169-1170. https://doi.org/10.1016/s0040-4039(98)02555-6
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