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
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
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
Calendar R, Berg P (1966) The catalytic properties of tyrosyl ribonucleic acid synthetases from Escherichia coli and Bacillus subtilis. Biochemistry 5:1690–1695
Chen Y, Chen C, Wu X (2012) Dicarbonyl reduction by single enzyme for the preparation of chiral diols. Chem Soc Rev 41:1742–1753
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
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
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
Hartman MC, Josephson K, Szostak JW (2006) Enzymatic aminoacylation of tRNA with unnatural amino acids. Proc Natl Acad Sci USA 103:4356–4361
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
Jakubowski H (1999) Misacylation of tRNALys with noncognate amino acids by lysyl-tRNA synthetase. Biochemistry 38:8088–8093
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
Liu CC, Schultz PG (2010) Adding new chemistries to the genetic code. Annu Rev Biochem 79:413–444
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
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
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
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
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
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
Wang L, Brock A, Herberich B, Schultz PG (2001) Expanding the genetic code of Escherichia coli. Science 292:498–500
Wang J, Schiller SM, Schultz PG (2007) A biosynthetic route to dehydroalanine-containing proteins. Angew Chem Int Ed Engl 46:6849–6851
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
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
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
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
Xie J, Schultz PG (2005) An expanding genetic code. Methods 36:227–238
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
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).
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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
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DOI: https://doi.org/10.1007/s00726-012-1311-1