Name: H-L-Lys(Poc)-OH*HCl
SKU: HAA2090
Availability: InStock

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250 mg

70,00 €

HAA2090.0250

500 mg

126,00 €

HAA2090.0500

1 g

196,00 €

HAA2090.0001

5 g

700,00 €

HAA2090.0005

25 g

2.800,00 €

HAA2090.0025

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description

H-L-Lys(Pryoc)-OH or H-L-Lys(EO-N3)-OH (HAA2080) are non-canonical amino acids suitable for click chemistry. They can be introduced site-specifically into recombinant proteins by the Pyrrolysyl-tRNA Synthetase/tRNA(CUA) Pair. Pyrrolysine (Pyl; HAA2830) is considered the 22nd proteinogenic amino acid. It is a naturally occurring, genetically coded amino acid used by some methanogenic archaea and one known bacterium in enzymes that are part of their methane-producing metabolism. It is similar to lysine, but with an added pyrroline ring linked to the end of the lysine side chain. It forms part of an unusual genetic code in these organisms.

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.

H-Lys(Poc)-OH is incorporated into proteins as an unnatural amino acid for further modifications using Click-chemistry.

references

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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

Click strategies for single-molecule protein fluorescence; S. Milles, S. Tyagi, N. Banterle, C. Koehler, V. VanDelinder, T. Plass, A. P. Neal and E. A. Lemke; J Am Chem Soc 2012; 134: 5187-95. https://doi.org/10.1021/ja210587q

Genetic encoding of a bicyclo[6.1.0]nonyne-charged amino acid enables fast cellular protein imaging by metal-free ligation; A. Borrmann, S. Milles, T. Plass, J. Dommerholt, J. M. Verkade, M. Wiessler, C. Schultz, J. C. van Hest, F. L. van Delft and E. A. Lemke; Chembiochem : a European journal of chemical biology 2012; 13: 2094-9. https://doi.org/10.1002/cbic.201200407

Expanding the genetic code of Drosophila melanogaster; A. Bianco, F. M. Townsley, S. Greiss, K. Lang and J. W. Chin; Nat Chem Biol 2012; 8: 748-50. https://doi.org/10.1038/nchembio.1043

Expanding the genetic code of an animal; S. Greiss and J. W. Chin; J Am Chem Soc 2011; 133: 14196-9. https://doi.org/10.1021/ja2054034

Encoding multiple unnatural amino acids via evolution of a quadruplet-decoding ribosome; H. Neumann, K. Wang, L. Davis, M. Garcia-Alai and J. W. Chin; Nature 2010; 464: 441-4. https://doi.org/10.1038/nature08817

A facile system for genetic incorporation of two different noncanonical amino acids into one protein in Escherichia coli; W. Wan, Y. Huang, Z. Wang, W. K. Russell, P. J. Pai, D. H. Russell and W. R. Liu; Angew Chem Int Ed Engl 2010; 49: 3211-4. https://doi.org/10.1002/anie.201000465

Expanding the genetic code of yeast for incorporation of diverse unnatural amino acids via a pyrrolysyl-tRNA synthetase/tRNA pair; S. M. Hancock, R. Uprety, A. Deiters and J. W. Chin; J Am Chem Soc 2010; 132: 14819-24. https://doi.org/10.1021/ja104609m

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

Pyrrolysine encoded by UAG in Archaea: charging of a UAG-decoding specialized tRNA; G. Srinivasan, C. M. James and J. A. Krzycki; Science 2002; 296: 1459-62. https://doi.org/10.1126/science.1069588

A new UAG-encoded residue in the structure of a methanogen methyltransferase; B. Hao, W. Gong, T. K. Ferguson, C. M. James, J. A. Krzycki and M. K. Chan; Science 2002; 296: 1462-6. https://doi.org/10.1126/science.1069556

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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