Skip to main content
SpringerLink
Log in

Incorporation of Noncoded Amino Acids by In Vitro Protein Biosynthesis

  • Chapter
  • First Online:
Implementation and Redesign of Catalytic Function in Biopolymers

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 202))

Abstract

The method of site-specific mutagenesis with noncoded amino acids using suppression of a nonsense codon by a semi-synthetic tRNA was first introduced in 1989. Initially used to probe the tolerance of the protein biosynthetic machinery for compounds other than the 20 primary amino acids, the method has since been applied to study a widely diverse range of biological problems. The ability to introduce side chains bearing subtle structural and electronic differences, fluorescent probes, isotope labels, photolabile protecting groups, chemical handles and photoactivated cross-linkers at unique sites has facilitated studies not currently accessible by other means. Improvements and alternatives to the early methodology are considered as well as some interesting recent applications.

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Winter G, Fersht AR, Wilkinson AJ, Zoller M, Smith M (1982) Nature 299:756

    Article  CAS  Google Scholar 

  2. Ulmer KM (1983) Science 219:666

    Article  CAS  Google Scholar 

  3. Glover DM, Hames BD (eds) (1995) DNA cloning: a practical approach, 2nd edn. IRL Press, New York

    Google Scholar 

  4. Kent SB, Baca M, Elder J, Miller M, Milton R, Milton S, Rao JMK, Schnolzer M (1995) Adv Exp Med Biol 362:425

    CAS  Google Scholar 

  5. Nyfeler R (1994) Methods Molec Biol 35:303

    CAS  Google Scholar 

  6. Muir TW, Kent SBH (1993) Curr Opin Biotechnol 4:420

    Article  CAS  Google Scholar 

  7. Humphries J, Offord RE, Smith RAG (1991) Curr Opin Biotechnol 2:539

    Article  CAS  Google Scholar 

  8. Offord RE (1987) Protein Eng 1:151

    Article  CAS  Google Scholar 

  9. Chaiken IM (1981) Crit Rev Biochem 11:255

    Article  CAS  Google Scholar 

  10. Gittel C, Schmidtchen FP (1995) Bioconjugate Chem 6:70

    Article  CAS  Google Scholar 

  11. Merkler DJ (1994) Enzyme Microb Technol 16:450

    Article  CAS  Google Scholar 

  12. Manning JM (1994) Methods Enzymol 231:225

    Article  CAS  Google Scholar 

  13. Matthews KS, Chakerian AE, Gardner JA (1991) Methods Enzymol 208:468

    Article  CAS  Google Scholar 

  14. Means GE, Feeney RE (1990) Bioconjugate Chem 1:2

    Article  CAS  Google Scholar 

  15. Means GE, Feeney RE (1971) Chemical modification of proteins. Holden-Day, San Francisco

    Google Scholar 

  16. Ross JBA, Szabo AG, Hogue CWV (1997) Methods Enzymol 278:151

    Article  CAS  Google Scholar 

  17. Wilson MJ, Hatfield DL (1984) Biochim Biophys Acta 781:205

    CAS  Google Scholar 

  18. Hortin G, Boime I (1983) Methods Enzymol 96:777

    Article  CAS  Google Scholar 

  19. Do H, Falcone D, Lin J, Andrews DW, Johnson AE (1996) Cell 85:369

    Article  CAS  Google Scholar 

  20. Mothes W, Prehn S, Rapoport TA (1994) EMBO J 13:3973

    CAS  Google Scholar 

  21. Johnson AE (1993) Trends Biochem Sci 18:456

    Article  CAS  Google Scholar 

  22. High S, Andersen SSL, Görlich D, Hartmann E, Prehn S, Rapoport TA, Dobberstein B (1993) J Cell Biol 121:743

    Article  CAS  Google Scholar 

  23. Bain JD, Glabe, CG, Dix, TA and Chamberlin, AR (1989) J Am Chem Soc 111:8013

    Article  CAS  Google Scholar 

  24. Bain JD, Diala ES, Glabe CG, Wacker DA, Lyttle MH, Dix TA, Chamberlin, AR (1991) Biochemistry 30:5411

    Article  CAS  Google Scholar 

  25. 9.(c) Bain JD, Wacker DA, Kuo Lyttle MH, Chamberlin AR (1991) J Org Chem 56:4615

    Article  CAS  Google Scholar 

  26. Noren CJ, Anthony-Cahill SJ, Griffith MC, Schultz PG (1989) Science 244:182

    Article  CAS  Google Scholar 

  27. Ellman J, Mendel D, Anthony-Cahill S, Noren CJ, Schultz PG (1991) Methods Enzymol 202:301

    Article  CAS  Google Scholar 

  28. Söll D (1988) Nature 331:662

    Article  Google Scholar 

  29. Murgola EJ (1995) Translational suppressors: when two wrongs DO make a right. In: Söll D, RajBhandary U (eds) tRNA: Structure, biosynthesis and function. ASM Press, Washington, DC, p 491

    Google Scholar 

  30. Hecht SM, Alford BL, Kuroda, Y, Kitano, SJ (1978) J Biol Chem 253:4517

    CAS  Google Scholar 

  31. Pezzuto JM, Hecht SM (1980) J Biol Chem 255:865

    CAS  Google Scholar 

  32. Heckler TG, Zama Y, Naka T, Hecht SM (1983) J Biol Chem 258:4492

    CAS  Google Scholar 

  33. Heckler TG, Chang LH, Zama Y, Naka T, Chorghade MS, Hecht SM (1984) Biochemistry 23:1468

    Article  CAS  Google Scholar 

  34. Heckler TG, Chang LH, Zama Y, Naka T, Hecht SM (1984) Tetrahedron 40:87

    Article  CAS  Google Scholar 

  35. Payne RC, Nichols BP, Hecht SM (1987) Biochemistry 26:3197

    Article  CAS  Google Scholar 

  36. Heckler TG, Roesser JR, Xu C, Chang P-I, Hecht SM (1988) Biochemistry 27:7254

    Article  CAS  Google Scholar 

  37. Roesser JR, Xu C, Payne RC, Surratt CK, Hecht SM (1989) Biochemistry 28:5185

    Article  CAS  Google Scholar 

  38. Baldini G, Martoglio B, Schachenmann A, Zugliani C, Brunner J (1988) Biochemistry 27:7951

    Article  CAS  Google Scholar 

  39. Englisch U, Gauss D, Freist W, Englisch S, Sternbach H, von der Haar F (1985) Angew Chem Int Ed Eng l24:1015

    Article  Google Scholar 

  40. Bain JD, Wacker DA, Kuo Lyttle MH, Chamberlin AR (1991) J Org Chem 56:4608

    Article  Google Scholar 

  41. Lyttle MH, Wright PB, Sinha ND, Bain JD, Chamberlin AR (1991) J Org Chem 56:4615

    Article  Google Scholar 

  42. Noren CJ, Anthony-Cahill JA, Suich DJ, Noren KA, Griffith MC, Schultz PG (1991) Nucleic Acids Res 18:83

    Article  Google Scholar 

  43. Steward LE, Chamberlin AR (1998) Methods Molec Biol 77:325

    CAS  Google Scholar 

  44. Ellman J, Mendel D, Anthony-Cahill S, Noren CJ, Schultz PG (1991) Methods Enzymol 202:301

    Article  CAS  Google Scholar 

  45. Caskey CT, Forrester WC, Tate W (1984) Peptide chain termination. In: Clark BFC, Petersen HU (eds) Gene expression: the translational step and its control. Munksgaard, Copenhagen

    Google Scholar 

  46. Bain JD, Switzer C, Chamberlin AR, Benner SA (1992) Nature 356:537

    Article  CAS  Google Scholar 

  47. Hatfield GW, Gurman GA (1992) Codon pair utilization bias in bacteria, yeast and mammals. In: Hatfield DL, Lee BJ, Pirtle RM (eds) Transfer RNA in protein synthesis. CRC Press, Boca Raton, chap 7

    Google Scholar 

  48. Noren CJ, Anthony-Cahill S, Suich DJ, Noren KA, Griffith MC, Schultz PG (1989) Nucl Acids Res 18:83

    Article  Google Scholar 

  49. Bain JD, Wacker DA, Kuo Chamberlin AR (1991) Tetrahedron 47:2389

    Article  CAS  Google Scholar 

  50. Hecht SM (1992) Acc Chem Res 25:545

    Article  CAS  Google Scholar 

  51. Mendel D, Cornish VW, Schultz PG (1995) Annu Rev Biophys Biomol Struct 24:435

    Article  CAS  Google Scholar 

  52. Cornish VW, Mendel D, Schultz PG (1995) Angew Chem Int Ed Engl 34:621

    Article  CAS  Google Scholar 

  53. Fahnestock S, Neuman H, Sashova V, Rich A (1970) Biochemistry 9:2477

    Article  CAS  Google Scholar 

  54. Scolnik E, Milman G, Rosman M, Caskey T (1970) Nature 225:152

    Article  Google Scholar 

  55. Fahnestock S, Rich A (1971) Science 173:340

    Article  CAS  Google Scholar 

  56. Pallanch L, Pak M, Schulman LH (1995) tRNA discrimination in aminoacylation. In: Soll D, RajBhandary U (eds) tRNA: structure, biosynthesis, and function. ASM Press, Washington, DC, chap 18

    Google Scholar 

  57. Fersht AR, Dingwall C (1979) Biochemistry 18:2627

    Article  CAS  Google Scholar 

  58. Rosa MD (1979) Cell 16:815

    Article  CAS  Google Scholar 

  59. Milligan JF, Groebe DR, Witherell GW, Uhlenbeck OC (1987) Nuc Acids Res 15:8783

    Article  CAS  Google Scholar 

  60. Steward LE (1996) PhD thesis, University of California, Irvine

    Google Scholar 

  61. Nowak MW, Kearney PC, Sampson JR, Saks ME, Labarca CG, Silverman SK, Zhong W, Thorson J, Abelson JN, Davidson N, Schultz PG, Dougherty DA, Lester HA (1995) Science 268:439

    Article  CAS  Google Scholar 

  62. Kearney PC, Nowak MW, Zhong W, Silverman SK, Lester HA, Dougherty DA (1996) Molecular Pharmacology 50:1401

    CAS  Google Scholar 

  63. Kearney PC, Zhang H, Zhong W, Dougherty DA, Lester HA (1996) Neuron 17:1221

    Article  CAS  Google Scholar 

  64. Saks M, Sampson JR, Nowak MW, Kearney PC, Du F, Abelson JN, Lester HA, Dougherty DA (1996) J Biol Chem 271:23169

    Article  CAS  Google Scholar 

  65. Cload ST, Liu DR, Froland WA, Schultz PG (1996) Chem & Biol 3:1033

    Article  CAS  Google Scholar 

  66. Kleina LG, Masson JM, Normanly J, Abelson J, Miller JH (1990) J Mol Biol 213:705

    Article  CAS  Google Scholar 

  67. Chg to a cross reference to Dougherty’s tRNA paper (1996)

    Google Scholar 

  68. Ting, AY, Shin I, Lucero C, Schultz PG (1998) J Am Chem Soc 120:7135

    Article  CAS  Google Scholar 

  69. Spirin AS (1986) Ribosome structure and protein biosynthesis. Benjamin/Cummings Publishing, Menlo Park

    Google Scholar 

  70. Tate WP, Brown CM (1992) Biochemistry 31:2443

    Article  CAS  Google Scholar 

  71. Benner SA (1994) Trends Biotechnol 12:158

    Article  CAS  Google Scholar 

  72. Zhouravleva G, Frolova L, Le Goff X, Le Guellec R, Inge-Vechtomov S, Kesselev L, Philippe M (1995) EMBO J 14:4065

    CAS  Google Scholar 

  73. Frolova L, Le Goff X, Zhouravleva G, Davydova E, Philippe M, Kisselev L (1996) RNA 2:334

    CAS  Google Scholar 

  74. Caskey CT (1998) Trends Biochem Sci 5:234

    Article  Google Scholar 

  75. Rydén SM, Isaksson LA (1984) Mol Gen Genet 193:38; Rydén M, Murphy J, Martin R, Isaksson L, Gallant J (1986) J Bacteriol 168:1066

    Article  Google Scholar 

  76. Rydén M, Murphy J, Martin R, Isaksson L, Gallant J (1986) J Bacteriol 168:1066

    Google Scholar 

  77. Pel HJ, Rep M, Grivell LA (1992) Nuc Acids Res 20:4423

    Article  CAS  Google Scholar 

  78. Moffat JG, Donly McCaughan KK, Tate WP (1993) J Biochem 213:749

    CAS  Google Scholar 

  79. Ma C, Kudlicki W, Odom OW, Kramer G, Hardesty B (1993) Biochemistry 32:7939

    Article  CAS  Google Scholar 

  80. Hohsaka T, Ashizuka Y, Murakami H, Sisido M (1996) J Am Chem Soc 118:9778

    Article  CAS  Google Scholar 

  81. Murakami H, Hohsaka T, Ashizuka Y, Sisido M (1998) J Am Chem Soc 120:7520

    Article  CAS  Google Scholar 

  82. Kanda T, Takai K, Yokoyama, Takaku H (1997) Nucleic Acids Symposium Series 37: 319

    Google Scholar 

  83. Kowal AK, Oliver JS (1997) Nucl Acids Res 25:4685

    Article  CAS  Google Scholar 

  84. Ohama T, Muto A, Osawa S (1990) Nucl Acids Res 18:1565

    Article  CAS  Google Scholar 

  85. Kano A, Andachi Y, Ohama T, Osawa S (1991) J Mol Biol 221:387

    Article  CAS  Google Scholar 

  86. Kano A, Ohama T, Abe R, Osawa S (1993) J Mol Biol 230:51

    Article  CAS  Google Scholar 

  87. Arslan T, Manaev SV, Mamaeva NV, Hecht SM (1997) J Am Chem Soc 119:10877

    Article  CAS  Google Scholar 

  88. Karginov VA, Mamaev SV, An H, Van Cleve MD, Hecht SM, Komatsoulis GA, Abelson N (1997) J Am Chem Soc 119:8166

    Article  CAS  Google Scholar 

  89. Karginov VA, Mamaev SV,Hecht SM (1997) Nuc Acids Res 25:3912

    Article  CAS  Google Scholar 

  90. Killian JA, Van Cleve MD, Shayo YF, Hecht SM (1998) J Am Chem Soc 120:3032

    Article  CAS  Google Scholar 

  91. Chapman E, Thorson JS, Schultz PG (1997) J Am Chem Soc 119:7151

    Article  CAS  Google Scholar 

  92. Koh JT, Cornish VW, Schultz PG (1997) Biochemistry 36:11314

    Article  CAS  Google Scholar 

  93. Thorson JS, Chapman E, Schultz PG (1995) J Am Chem Soc 117:9361

    Article  CAS  Google Scholar 

  94. High S, Martoglio B, Gorlich D, Andersen SSL, Ashford AJ, Giner A, Hartmann E, Prehn S, Rapoport TA, Dobberstein B, Brunner J (1993) J Biol Chem 268:26745

    CAS  Google Scholar 

  95. Martoglio B, Hofmann MW, Brunner J, Dobberstein B (1995) Cell 81:207

    Article  CAS  Google Scholar 

  96. Sonar S, Lee CP, Coleman M, Patel N, Liu X, Marti T, Khorana HG, RajBhandary UL, Rothschild KJ (1994) Nature Struct Biol 1:512

    Article  CAS  Google Scholar 

  97. Ludlam CFC, Sonar S, Lee C-P, Coleman M, Herzfeld J, RajBhandary UL, Rothschild KJ (1995) Biochemistry 34:2

    Article  CAS  Google Scholar 

  98. Liu X-M, Sonar S, Lee C-P, Coleman M, RajBhandary UL, Rothschild KJ (1995) Biophys Chem 56:63

    Article  CAS  Google Scholar 

  99. Kearney PC, Zhang H, Zhong W, Dougherty DA, Lester HA (1996) Neuron 17:1221

    Article  CAS  Google Scholar 

  100. England PM, Lester HA, Davidson N, Dougherty DA (1997) Proc Natl Acad Sci USA 94:11025

    Article  CAS  Google Scholar 

  101. Miller JC, Silverman SK, England PM, Dougherty DA, Lester HA (1998) Neuron 20:619

    Article  CAS  Google Scholar 

  102. Turcatti G, Nemeth K, Edgerton MD, Meseth U, Talabot F, Peitsch M, Knowles J, Vogel H, Chollet A (1996) J Biol Chem 271:19991

    Article  CAS  Google Scholar 

  103. Steward LE, Collins CS, Gilmore MA, Carlson JE, Ross JBA, Chamberlin AR (1997) J Am Chem Soc 119:6

    Article  CAS  Google Scholar 

  104. Park Y, Luo J, Schultz PG, Kirsch JF (1997) Biochemistry 36:10517

    Article  CAS  Google Scholar 

  105. Murakami H, Hohsaka T, Ashizuka Y, Sisido M (1998) J Am Chem Soc 120:7520

    Article  CAS  Google Scholar 

  106. Zhao Z, Liu X, Shi Z, Danley L, Huang B, Jiang R-T, Tsai M-D (1996) J Am Chem Soc 118: 3535

    Article  CAS  Google Scholar 

Download references

Author information

Author notes

  1. Lance E. Steward

    Present address: Department of Chemistry, University of Utah, Salt Lake City, UT, 84112, USA

Authors and Affiliations

  1. Department of Chemistry, University of California, Irvine, CA, 92697, USA

    Marcella A. Gilmore, Lance E. Steward & A. Richard Chamberlin

Authors
  1. Marcella A. Gilmore
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Lance E. Steward
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. Richard Chamberlin
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Institut für Organische Chemie und Biochemie, Technische Universität München, D-85747, Garching, Germany

    Franz P. Schmidtchen

Rights and permissions

Reprints and permissions

Copyright information

© 1999 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Gilmore, M.A., Steward, L.E., Chamberlin, A.R. (1999). Incorporation of Noncoded Amino Acids by In Vitro Protein Biosynthesis. In: Schmidtchen, F.P., et al. Implementation and Redesign of Catalytic Function in Biopolymers. Topics in Current Chemistry, vol 202. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-48990-8_3

Download citation

  • DOI: https://doi.org/10.1007/3-540-48990-8_3

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-65728-6

  • Online ISBN: 978-3-540-48990-0

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation