Skip to main content
Log in

Genetic incorporation of d-lysine into diketoreductase in Escherichia coli cells

  • Short Communication
  • Published:
Amino Acids Aims and scope Submit manuscript

Abstract

Pyrococcus horikoshii lysyl-tRNA synthetase/tRNA orthogonal pair exhibited high selectivity towards d-lysine in the presence of excess amount of d-lysine. Based on the observation, this orthogonal pair was employed to encode d-lysine, and d-lysine was site-specifically incorporated into the diketoreductase in E. coli cells.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

References

  • Anderson JC, Wu N, Santoro SW, Lakshman V, King DS, Schultz PG (2004) An expanded genetic code with a functional quadruplet codon. Proc Natl Acad Sci USA 101:7566–7571

    Article  PubMed  CAS  Google Scholar 

  • Anderson JC, Wu N, Santoro S, Schultz PG (2006) Compositions of orthogonal lysyl-tRNA and aminoacyl-tRNA synthetase pairs. US patent, US7575895B2

  • Bhuta A, Quiggle K, Ott T, Ringer D, Chládek S (1981) Stereochemical control of ribosomal peptidyltransferase reaction. Role of amino acid side-chain orientation of acceptor substrate. Biochemistry 20:8–15

    Article  PubMed  CAS  Google Scholar 

  • Calendar R, Berg P (1966) The catalytic properties of tyrosyl ribonucleic acid synthetases from Escherichia coli and Bacillus subtilis. Biochemistry 5:1690–1695

    Article  PubMed  CAS  Google Scholar 

  • Chen Y, Chen C, Wu X (2012) Dicarbonyl reduction by single enzyme for the preparation of chiral diols. Chem Soc Rev 41:1742–1753

    Article  PubMed  CAS  Google Scholar 

  • Dedkova LM, Fahmi NE, Golovine SY, Hecht SM (2003) Enhanced d-amino acid incorporation into protein by modified ribosomes. J Am Chem Soc 125:6616–6617

    Article  PubMed  CAS  Google Scholar 

  • Fujii N, Kawaguchi T, Sasaki H, Fujii N (2011) Simultaneous stereoinversion and isomerization at the Asp-4 residue in βB2-crystallin from the aged human eye lenses. Biochemistry 50:8628–8635

    Article  PubMed  CAS  Google Scholar 

  • Gilreath MS, Roy H, Bullwinkle TJ, Katz A, Navarre WW, Ibba M (2011) β-Lysine discrimination by lysyl-tRNA synthetase. FEBS Lett 585:3284–3288

    Article  PubMed  CAS  Google Scholar 

  • Hartman MC, Josephson K, Szostak JW (2006) Enzymatic aminoacylation of tRNA with unnatural amino acids. Proc Natl Acad Sci USA 103:4356–4361

    Article  PubMed  CAS  Google Scholar 

  • Huang Y, Lu Z, Liu N, Chen Y (2012) Identification of important residues in diketoreductase from Acinetobacter baylyi by molecular modeling and site-directed mutagenesis. Biochimie 94:471–478

    Article  PubMed  CAS  Google Scholar 

  • Jakubowski H (1999) Misacylation of tRNALys with noncognate amino acids by lysyl-tRNA synthetase. Biochemistry 38:8088–8093

    Article  PubMed  CAS  Google Scholar 

  • Krause E, Bienert M, Schmieder P, Wenschuh H (2000) The helix-destabilizing propensity scale of d-amino acids:  the influence of side chain steric effects. J Am Chem Soc 122:4865

    Article  CAS  Google Scholar 

  • Liu CC, Schultz PG (2010) Adding new chemistries to the genetic code. Annu Rev Biochem 79:413–444

    Article  PubMed  CAS  Google Scholar 

  • Lu M, Cao X, Yang X, Zheng H, Liu N, Jiang Y, Lin D, Chen Y (2010) A diketoreductase exhibits unique renaturation profile from thermal-induced protein unfolding. Amino Acids 39:609–613

    Article  PubMed  CAS  Google Scholar 

  • Miyamoto T, Sekine M, Ogawa T, Hidaka M, Homma H, Masaki H (2010) Detection of d-amino acids in purified proteins synthesized in Escherichia coli. Amino Acids 38:1377–1385

    Article  PubMed  CAS  Google Scholar 

  • Soutourina J, Plateau P, Blanquet S (2000) Metabolism of d-aminoacyl-tRNAs in Escherichia coli and Saccharomyces cerevisiae cells. J Biol Chem 275:32535–32542

    Article  PubMed  CAS  Google Scholar 

  • Soutourina O, Soutourina J, Blanquet S, Plateau P (2004) Formation of d-tyrosyl-tRNATyr accounts for the toxicity of d-tyrosine toward Escherichia coli. J Biol Chem 279:42560–42565

    Article  PubMed  CAS  Google Scholar 

  • Takayama T, Ogawa T, Hidaka M, Shimizu Y, Ueda T, Masaki H (2005) Esterification of Escherichia coli tRNAs with d-histidine and d-lysine by aminoacyl-tRNA synthetases. Biotechnol Biochem Biosci 69:1040–1041

    Article  CAS  Google Scholar 

  • Terada T, Nureki O, Ishitani R, Ambrogelly A, Ibba M, Söll D, Yokoyama S (2002) Functional convergence of two lysyl-tRNA synthetases with unrelated topologies. Nat Struct Biol 9:257–262

    Article  PubMed  CAS  Google Scholar 

  • Wang L, Brock A, Herberich B, Schultz PG (2001) Expanding the genetic code of Escherichia coli. Science 292:498–500

    Article  PubMed  CAS  Google Scholar 

  • Wang J, Schiller SM, Schultz PG (2007) A biosynthetic route to dehydroalanine-containing proteins. Angew Chem Int Ed Engl 46:6849–6851

    Article  PubMed  CAS  Google Scholar 

  • Wu X, Liu N, He Y, Chen Y (2008) A bacterial enzyme catalyzing double reduction of β, δ-diketo ester with unprecedented stereoselectivity. Nat Preced. http://hdl.handle.net/10101/npre.12008.11697.10101

  • Wu X, Liu N, He Y, Chen Y (2009) Cloning, expression, and characterization of a novel diketoreductase from Acinetobacter baylyi. Acta Biochim Biophys Sin (Shanghai) 41:163–170

    Article  CAS  Google Scholar 

  • Wu X, Wang L, Wang S, Chen Y (2010) Stereoselective introduction of two chiral centers by a single diketoreductase: an efficient biocatalytic route for the synthesis of statin side chains. Amino Acids 39:305–308

    Article  PubMed  CAS  Google Scholar 

  • Wu X, Chen C, Liu N, Chen Y (2011a) Preparation of ethyl 3R,5S-6-(benzyloxy)-3,5-dihydroxy-hexanoate by recombinant diketoreductase in a biphasic system. Bioresour Technol 102:3649–3652

    Article  PubMed  CAS  Google Scholar 

  • Wu X, Jiang J, Chen Y (2011b) Correlation between intracellular cofactor concentrations and biocatalytic efficiency: coexpression of diketoreductase and glucose dehydrogenase for the preparation of chiral diol for statin drugs. ACS Catal 1:1661–1664

    Article  CAS  Google Scholar 

  • Xie J, Schultz PG (2005) An expanding genetic code. Methods 36:227–238

    Article  PubMed  CAS  Google Scholar 

  • Young DD, Jockush S, Turro NJ, Schultz PG (2011) Synthetase polyspecificity as a tool to modulate protein function. Bioorg Med Chem Lett 21:7502–7504

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgments

We are grateful for the technical assistance from Zhijuan Xu and Hairong Ma. This work was supported by “111 project” from the Ministry of Education of China and the State Administration of Foreign Export Affairs of China (No: 111-2-07) and the Innovation Fund Project for Graduate Students of Jiangsu Province (CXLX11-0796).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yijun Chen.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 1065 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Liu, Z., Yang, X., Yi, D. et al. Genetic incorporation of d-lysine into diketoreductase in Escherichia coli cells. Amino Acids 43, 2553–2559 (2012). https://doi.org/10.1007/s00726-012-1311-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00726-012-1311-1

Keywords

Navigation