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Fmoc-L-Lys(Pryoc)-OH
Chemical name: (S)-2-((9-Fluorenylmethyloxyl)amino)-6-((prop-2-ynyloxy)carbonylamino)hexanoic acid // Synonyms: N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-epsilon-(prop-2-ynyloxycarbonyl)-L-lysine, Fmoc-Lys(Pryoc)-OH, Fmoc-Lys(Proc)-OH, Fmoc-Lys(Pryoc)-OH
- Product code:FAA3150
- CAS No.:1584133-25-4
- Formula:C25H26N2O6
- Storage temperature:2-8°C
- Molecular weight:450.48 g/mol
- Purity :min. 98%
- Enantiomeric Purity:min. 99.7%
from $135.00
description
tRNA can be loaded with the propargyl analogue of free L-lysine by pyrrolysyl-tRNA synthetase enabling the biochemist to introduce site specifically an alkyne group into a protein for further click conjugation.
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
Genetic encoding and labeling of aliphatic azides and alkynes in recombinant proteins via a pyrrolysyl-tRNA Synthetase/tRNA(CUA) pair and click chemistry; D. P. Nguyen, H. Lusic, H. Neumann, P. B. Kapadnis, A. Deiters and J. W. Chin; J Am Chem Soc 2009; 131: 8720-1. https://doi.org/10.1021/ja900553w
Direct charging of tRNACUA with pyrrolysine in vitro and in vivo; S. K. Blight, R. C. Larue, A. Mahapatra, D. G. Longstaff, E. Chang, G. Zhao, P. T. Kang, K. B. Green-Church, M. K. Chan and J. A. Krzycki; Nature 2004; 431: 333. https://doi.org/10.1038/nature02895
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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