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From the Prebiotic Synthesis of α-Amino Acids Towards a Primitive Translation Apparatus for the Synthesis of Peptides

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Book cover Prebiotic Chemistry

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 259))

Abstract

The demonstration that ribosomal peptide synthesis is a ribozyme-catalyzed reaction does not establish that amino acids and peptides have been useless and/or missing in an RNA world. The prebiotic chemistry of amino acids and peptides thus remains an important field of investigation. We first review the literature on amino acid synthesis and then focus on the topic of peptide synthesis pathways. Most proposed pathways are examined in the context of the thermodynamic constraints on peptide bond formation and using yet unpublished evaluations of the free energy contents of activated intermediates. This analysis provides evidences in favor of an important role of α-amino acid N-carboxyanhydrides (NCAs) as activated peptide monomers and possibly as early free energy carriers owing to their ability to activate inorganic phosphate and nucleotides. Finally, the transition towards the emergence of the biochemical amino acid activation pathways involving amino acid-phosphoric acid mixed anhydrides via both ribosomal and non-ribosomal processes is analyzed from the perspective that life emerged through a coevolution linking amino acid and nucleotide chemistries.

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Abbreviations

AA:

α-amino acid

CAA:

N-carbamoyl α-amino acid (α-ureido acid)

CDI:

N,N′-carbonyldiimidazole

NCA:

amino acid-N-carboxyanhydride; N-carboxy-amino acid anhydride

PNA:

peptide nucleic acid [-20pt]

References

  1. Miller SL (1953) Science 117:528

    PubMed  Google Scholar 

  2. Bada JL, Lazcano A (2003) Science 300:745

    Article  PubMed  Google Scholar 

  3. Lazcano A, Bada JL (2003) Origins Life Evol Biosphere 33:235

    Article  Google Scholar 

  4. Pizzarello S (2004) Origins Life Evol Biosphere 34:25

    Article  Google Scholar 

  5. Stubbe J (2000) Curr Opin Struct Biol 10:731

    Article  PubMed  Google Scholar 

  6. Szathmary E (1993) Proc Natl Acad Sci USA 90:9916

    PubMed  Google Scholar 

  7. Szathmary E (1999) Trends Genet 15:223

    Article  PubMed  Google Scholar 

  8. Cech TR (1990) Angew Chem Int Ed 29:759

    Article  Google Scholar 

  9. Altman S (1990) Angew Chem Int Ed 29:749

    Article  Google Scholar 

  10. Orgel LE (1968) J Mol Biol 38:381–393

    Article  PubMed  Google Scholar 

  11. White HB (1976) J Mol Evol 7:101

    Article  PubMed  Google Scholar 

  12. Gilbert W (1986) Nature 319:618

    Article  Google Scholar 

  13. Gesteland RF, Cech TR, Atkins JF (1999) The RNA World, 2nd edn. Cold Spring Harbor Laboratory Press, New York

    Google Scholar 

  14. Orgel LE (2004) Crit Rev Biochem Mol Biol 39:99

    Article  PubMed  Google Scholar 

  15. Orgel LE (1998) Trends Biochem Sci 23:491

    Article  PubMed  Google Scholar 

  16. Noller HF, Hoffarth V, Zimniak L (1992) Science 256:1416

    PubMed  Google Scholar 

  17. Nissen P, Hansen J, Ban N, Moore PB, Steitz TA (2000) Science 289:920

    Article  PubMed  Google Scholar 

  18. Nielsen PE (1993) Origins Life Evol Biosphere 23:323

    Article  Google Scholar 

  19. Böhler C, Nielsen PE, Orgel LE (1995) Nature 376:578

    Article  PubMed  Google Scholar 

  20. Nelson KE, Levy M, Miller SL (2000) Proc Natl Acad Sci USA 97:3868

    Article  PubMed  Google Scholar 

  21. Lacey JC, Weber AL, White WE (1975) Origins Life 6:273

    Article  Google Scholar 

  22. Borsenberger V, Crowe MA, Lehbauer J, Raftery J, Helliwell M, Bhutia K, Cox T, Sutherland JD (2004) Chem Biodiversity 1:203

    Article  Google Scholar 

  23. Smith JM, Borsenberger V, Raftery J, Sutherland JD (2004) Chem Biodiversity 1:1418

    Article  Google Scholar 

  24. Tan B, Lee MC, Cui M, Liu T, Chen Z-Z, Li Y-M, Ju Y, Zhao Y-F, Chen K, Jiang H-L (2004) J Mol Struct (Theochem) 672:51

    Article  Google Scholar 

  25. Di Giulio M (1997) J Mol Evol 45:571

    PubMed  Google Scholar 

  26. Cavalier-Smith T (2001) J Mol Evol 53:555

    Article  PubMed  Google Scholar 

  27. Weber AL (2002) Origins Life Evol Biosphere 32:333

    Article  Google Scholar 

  28. Nicolis G, Prigogine I (1977) Self-Organization in Nonequilibrium Systems. Wiley, New York

    Google Scholar 

  29. Martin H (2005) In: Gargaud M, Barbier B, Martin H, Reisse J (eds) Lectures in Astrobiology – Part I: The Early Earth and Other Cosmic Habitats for Life (Advances in Astrobiology and Biogeophysics). Springer, Berlin Heidelberg New York, p 91

    Google Scholar 

  30. Kasting JF (1993) Science 259:920

    PubMed  Google Scholar 

  31. Chyba CF, Sagan C (1992) Nature 355:125

    Article  PubMed  Google Scholar 

  32. Bauer SJ (2002) Eur Space Agency, Special Publication SP-518:21

    Google Scholar 

  33. Miller SL (1955) J Am Chem Soc 77:2351

    Article  Google Scholar 

  34. Strecker A (1850) Liebigs Ann Chem 75:27

    Google Scholar 

  35. Schlesinger G, Miller SL (1973) J Am Chem Soc 95:3729

    Article  Google Scholar 

  36. Taillades J, Commeyras A (1974) Tetrahedron 30:127

    Article  Google Scholar 

  37. Taillades J, Commeyras A (1974) Tetrahedron 30:2493

    Article  Google Scholar 

  38. Taillades J, Commeyras A (1974) Tetrahedron 30:3407

    Article  Google Scholar 

  39. Béjaud M, Mion L, Commeyras A (1976) Bull Soc Chim Fr:1425

    Google Scholar 

  40. Moutou G, Taillades J, Bénefice-Malouet S, Commeyras A, Messina G, Mansani R (1995) J Phys Org Chem 8:721

    Article  Google Scholar 

  41. Miller SL, Van Trump JE (1981) In: Wolman Y (ed) Origin of life. Reidel, Dordrecht, p 135

    Google Scholar 

  42. Pascal R, Taillades J, Commeyras A (1980) Tetrahedron 36:2999

    Article  Google Scholar 

  43. Taillades J, Beuzelin I, Garrel L, Tabacik V, Bied C, Commeyras A (1998) Origins Life Evol Biosphere 28:61

    Article  Google Scholar 

  44. Pascal R (2003) Eur J Org Chem:1813

    Google Scholar 

  45. Jencks WP (1975) Adv Enzymol Relat Areas Mol Biol 43:219

    PubMed  Google Scholar 

  46. Bergs H (1929) German Patent 566.094

    Google Scholar 

  47. Rousset A, Lasperas M, Taillades J, Commeyras A (1980) Tetrahedron 36:2649

    Article  Google Scholar 

  48. Taillades J, Rousset A, Lasperas M, Commeyras A (1986) Bull Soc Chim Fr:650

    Google Scholar 

  49. Blagoeva IB, Pojarlieff IG, Dimitrof VS (1978) J Chem Soc Perkin Trans II:887

    Google Scholar 

  50. Yamagata Y, Mori T (1982) Origins Life 12:41

    Article  Google Scholar 

  51. Commeyras A, Boiteau L, Vandenabeele-Trambouze O, Selsis F (2005) In: Gargaud M, Barbier B, Martin H, Reisse J (eds) Lectures in Astrobiology – Part II: From Prebiotic Chemistry to the Origins of Life on Earth (Advances in Astrobiology and Biogeophysics). Springer, Berlin Heidelberg New York, p 501

    Google Scholar 

  52. Hennet RJC, Holm NG, Engel MH (1992) Naturwissenschaften 79:361

    Article  Google Scholar 

  53. Marshall WL (1994) Geochim Cosmochim Acta 58:2099

    Article  Google Scholar 

  54. Alargov DK, Deguchi S, Tsujii K, Horikoshi K (2002) Origins Life Evol Biosphere 32:1

    Article  Google Scholar 

  55. Kobayashi K, Kohara M, Dokiya M, Yanagawa H (1997) Viva Origino 25:167

    Google Scholar 

  56. Islam MN, Kaneko T, Kobayashi K (2003) Bull Chem Soc Jpn 76:1171

    Article  Google Scholar 

  57. Kobayashi K, Kaneko T, Saito T, Oshima T (1998) Origins Life Evol Biosphere 28:155

    Article  Google Scholar 

  58. Kobayashi K, Kaneko T, Saito T (1999) Adv Space Res 24:461

    Article  PubMed  Google Scholar 

  59. Kobayashi K, Masuda H, Ushio K-I, Ohashi A, Yamanashi H, Kaneko T, Takahashi J-I, Hosokawa T, Hashimoto H, Saito T (2001) Adv Space Res 27:207

    Article  PubMed  Google Scholar 

  60. Plankensteiner K, Reiner H, Schranz B, Rode BM (2004) Angew Chem Int Ed 43:1886

    Article  Google Scholar 

  61. Weber AL (1998) Origins Life Evol Biosphere 28:259

    Article  Google Scholar 

  62. Weber AL (2001) Origins Life Evol Biosphere 31:71

    Article  Google Scholar 

  63. Cronin JR (1998) In: Brack A (ed) The molecular origins of life. Cambridge University Press, Cambridge, p 119

    Google Scholar 

  64. Cronin JR, Chang S (1993) In: Greenberg JM, Mendoza-Gomez CX, Pirronello V (eds) The Chemistry of Life's Origins. Kluwer, Dordrecht, p 209

    Google Scholar 

  65. Shimoyama A, Ogasawara R (2002) Origins Life Evol Biosphere 32:165

    Article  Google Scholar 

  66. Cooper GW, Cronin JR (1995) Geochim Cosmochim Acta 59:1003

    Article  PubMed  Google Scholar 

  67. Meierhenrich UJ, Munoz Caro GM, Bredehoeft JH, Jessberger EK, Thiemann WHP (2004) Proc Natl Acad Sci USA 101:9182

    Article  PubMed  Google Scholar 

  68. Pizzarello S, Cooper GW (2001) Meteorit Planet Sci 36:897

    Google Scholar 

  69. Cronin JR, Pizzarello S (1997) Science 275:951

    Article  PubMed  Google Scholar 

  70. Pizzarello S, Cronin JR (2000) Geochim Cosmochim Acta 64:329

    Article  PubMed  Google Scholar 

  71. Pizzarello S, Zolensky M, Turk KA (2003) Geochim Cosmochim Acta 67:1589

    Article  Google Scholar 

  72. Crisma M, Moretto A, Formaggio F, Kaptein B, Broxterman QB, Toniolo C (2004) Angew Chem Int Ed 43:6695–6699

    Article  Google Scholar 

  73. Pizzarello S, Weber AL (2004) Science 303:1151

    Article  PubMed  Google Scholar 

  74. Maurette M (1998) Origins Life Evol Biosphere 28:385

    Article  Google Scholar 

  75. Brinton KLF, Engrand C, Glavin DP, Bada JL, Maurette M (1998) Origins Life Evol Biosphere 28:413

    Article  Google Scholar 

  76. Maurette M, Duprat J, Engrand C, Gounelle M, Kurat G, Matrajt G, Toppani A (2000) Planet Sp Sci 48:1117

    Article  Google Scholar 

  77. Snyder LE (1997) Origins Life Evol Biosphere 27:115

    Article  Google Scholar 

  78. Sorrell WH (1997) Astrophys Space Sci 253:27

    Article  Google Scholar 

  79. Kuan Y-J, Charnley SB, Huang H-C, Tseng W-L, Kisiel Z (2003) Astrophys J 593:848

    Article  Google Scholar 

  80. Charnley SB, Ehrenfreund P, Kuan Y-J (2003) Physics World 16:35

    Google Scholar 

  81. Walch SP, Bauschlicher CWJ, Ricca A, Bakes ELO (2001) Chem Phys Lett 333:6

    Article  Google Scholar 

  82. Mendoza C, Ruette F, Martorell G, Rodriguez LS (2004) Astrophys J 601:L59

    Article  Google Scholar 

  83. Takahashi J-I, Hosokawa T, Masuda H, Kaneko T, Kobayashi K, Saito T, Utsumi Y (1999) Appl Phys Lett 74:877

    Article  Google Scholar 

  84. Takano Y, Masuda H, Kaneko T, Kobayashi K (2002) Chem Lett:986

    Google Scholar 

  85. Munoz Caro GM, Meierhenrich UJ, Schutte WA, Barbier B, Segovia AA, Rosenbauer H, Thiemann WHP, Brack A, Greenberg JM (2002) Nature 416:403

    Article  PubMed  Google Scholar 

  86. Bernstein MP, Dworkin JP, Sandford SA, Cooper GW, Allamandola LJ (2002) Nature 416:401

    Article  PubMed  Google Scholar 

  87. Kobayashi K, Kasamatsu T, Kaneko T, Koike J, Oshima T, Saito T, Yamamoto T, Yanagawa H (1995) Adv Space Res 16:21

    Article  PubMed  Google Scholar 

  88. Kasamatsu T, Kaneko T, Saito T, Kobayashi K (1997) Bull Chem Soc Jpn 70:1021

    Google Scholar 

  89. Takano Y, Ushio K, Kaneko T, Kobayashi K, Hashimoto H (2003) Chem Lett 32:612

    Article  Google Scholar 

  90. Devienne FM, Barnabé C, Couderc M, Ourisson G (1998) C R Acad Sci Paris, Serie IIc 1:435

    Google Scholar 

  91. Devienne FM, Barnabé C, Ourisson G (2002) C R Chimie 5:651

    Google Scholar 

  92. Ehrenfreund P, Bernstein MP, Dworkin JP, Sandford SA, Allamandola LJ (2001) Astrophys J 550:L95

    Article  Google Scholar 

  93. Schwell M, Dulieu F, Leach S (2001) Eur Space Agency, Special Publication SP-496:133

    Google Scholar 

  94. Barbier B, Chabin A, Chaput D, Brack A (1998) Planet Sp Sci 46:391

    Article  Google Scholar 

  95. Boillot F, Chabin A, Bure C, Venet M, Belsky A, Bertrand-Urbaniak M, Delmas A, Brack A, Barbier B (2002) Origins Life Evol Biosphere 32:359

    Article  Google Scholar 

  96. Barbier B, Coll P, Cottin H, Leach S, Maurel M-C, Raulin F, Tepfer D, Brack A (2002) Eur Space Agency, Special Publication SP-518:59

    Google Scholar 

  97. Basiuk VA, Douda J, Navarro-Gonzalez R (1999) Adv Space Res 24:505

    Article  PubMed  Google Scholar 

  98. Basiuk VA, Navarro-Gonzalez R, Basiuk EV (1998) Origins Life Evol Biosphere 28:167

    Article  Google Scholar 

  99. Brack A, Barbier B, Bertrand M, Chabin A, Westall F (2002) Eur Space Agency, Special Publication SP-518:435

    Google Scholar 

  100. Jakubke H-D, Kuhl P, Könnecke A (1985) Angew Chem Int Ed 24:85

    Article  Google Scholar 

  101. Ivanov IP, Todorov NP, Petkov DD (1993) Tetrahedron 49:2307

    Article  Google Scholar 

  102. Jencks WP (1976) In: Fasman GD (ed) Handbook of Biochemistry and Molecular Biology, 3rd edn, Vol I Physical and Chemical Data. CRC Press, Cleveland, p 296

    Google Scholar 

  103. Smith RM, Hansen DE (1998) J Am Chem Soc 120:8910

    Article  Google Scholar 

  104. Radzicka A, Wolfenden R (1996) J Am Chem Soc 118:6105

    Article  Google Scholar 

  105. Corey MJ, Corey E (1996) Proc Natl Acad Sci USA 93:11428

    Article  PubMed  Google Scholar 

  106. Lahav N, White D, Chang S (1978) Science 201:67

    PubMed  Google Scholar 

  107. Flegmann AW, Tattersall R (1979) J Mol Evol 12:349

    Article  PubMed  Google Scholar 

  108. Rode BM (1999) Peptides 20:773

    Article  PubMed  Google Scholar 

  109. Kirby AJ (1980) Adv Phys Org Chem 17:183

    Google Scholar 

  110. Plankensteiner K, Righi A, Rode BM (2002) Origins Life Evol Biosphere 32:225

    Article  Google Scholar 

  111. Bujdak J, Rode BM (1999) Origins Life Evol Biosphere 29:451

    Article  Google Scholar 

  112. Bujdak J, Rode BM (1999) J Mol Catal A: Chem 144:129

    Article  Google Scholar 

  113. Rode BM, Son HL, Suwannachot Y, Bujdak J (1999) Origins Life Evol Biosphere 29:273

    Article  Google Scholar 

  114. Porter TL, Eastman MP, Hagerman ME, Price LB, Shand RF (1998) J Mol Evol 47:373

    PubMed  Google Scholar 

  115. Li Y-M, Yin Y-W, Zhao Y-F (1992) Int J Pept Protein Res 39:375

    PubMed  Google Scholar 

  116. Zhao Y-F, Cao P-S (1994) J Biol Phys 20:283

    Google Scholar 

  117. Ju Y, Zhao Y-F, Sha Y-W, Tan B (1995) Phosphorus Sulfur Silicon 101:117

    Google Scholar 

  118. Zhou W, Ju Y, Zhao Y-F, Wang Q, Luo G (1996) Origins Life Evol Biosphere 26:547

    Article  Google Scholar 

  119. Zhao Y-F, Cao P-S (1996) In: Chela-Flores J, Raulin F (eds) Chemical Evolution: Physics of the Origin and Evolution of Life (Proceedings of the 4th Trieste Conference on Chemical Evolution, Trieste, Sept. 4–8, 1995). Kluwer, Dordrecht, p 279

    Google Scholar 

  120. Zhao Y-F, Cao P-S (1999) Pure Appl Chem 71:1163

    Google Scholar 

  121. Fu H, Han B, Zhao Y-F, Tu G-Z, Xu L, Lu Q, Wang J-Z, Xiao H-Z (2003) Bioorg Chem 31:122

    Article  PubMed  Google Scholar 

  122. Cheng CM, Liu XH, Li Y-M, Ma Y, Tan B, Wan R, Zhao Y-F (2004) Origins Life Evol Biosphere 34:455

    Article  Google Scholar 

  123. Chen Z-Z, Tan B, Li Y-M, Zhao Y-F (2003) J Org Chem 68:4052

    PubMed  Google Scholar 

  124. Kricheldorf HR (1987) α-Aminoacid-N-Carboxy-Anhydrides and Related Heterocycles. Springer, Berlin Heidelberg New York

    Google Scholar 

  125. Blair NE, Bonner WA (1980) Origins Life 10:255

    Article  Google Scholar 

  126. Ehler KW (1976) J Org Chem 41:3041

    Article  Google Scholar 

  127. Brack A (1987) Origins Life 17:367

    Google Scholar 

  128. Hessler AM, Lowe DR, Jones RL, Bird DK (2004) Nature 428:736

    Article  PubMed  Google Scholar 

  129. Ferris JP, Hill AR, Liu R, Orgel LE (1996) Nature 381:59

    Article  PubMed  Google Scholar 

  130. Jencks WP (1981) Proc Natl Acad Sci USA 78:4046

    Google Scholar 

  131. Page MI, Jencks WP (1971) Proc Natl Acad Sci USA 68:1678

    PubMed  Google Scholar 

  132. Mandolini L (1986) Adv Phys Org Chem 22:1

    Google Scholar 

  133. Cacciapaglia R, Di Stefano S, Mandolini L (2004) Acc Chem Res 37:113

    Article  PubMed  Google Scholar 

  134. Wieland T, Jaenicke F (1956) Liebigs Ann Chem 599:125

    Google Scholar 

  135. Hay RW, Main L (1968) Aust J Chem 21:155

    Google Scholar 

  136. Brack A (1982) Biosystems 15:201

    Article  PubMed  Google Scholar 

  137. Lacey JC, Senaratne N, Mullins DW (1984) Origins Life 15:45

    Article  Google Scholar 

  138. Mullins DW, Senaratne N, Lacey JC (1984) Origins Life 14:597

    Article  Google Scholar 

  139. Paecht-Horowitz M, Berger J, Katchalsky A (1970) Nature 228:636

    Article  PubMed  Google Scholar 

  140. Armstrong DW, Seguin R, McNeal CJ, Macfarlane RD, Fendler JH (1978) J Am Chem Soc 100:4605

    Article  Google Scholar 

  141. Williams A, Douglas KT (1975) Chem Rev 75:627

    Article  Google Scholar 

  142. Hegarty AF, Frost LN, Coy JH (1974) J Org Chem 39:1089

    Article  Google Scholar 

  143. Collet H, Bied C, Mion L, Taillades J, Commeyras A (1996) Tetrahedron Lett 37:9043

    Article  Google Scholar 

  144. Taillades J, Collet H, Garrel L, Beuzelin I, Boiteau L, Choukroun H, Commeyras A (1999) J Mol Evol 48:638

    PubMed  Google Scholar 

  145. Collet H, Garrel L, Commeyras A, unpublished results

    Google Scholar 

  146. Commeyras A, Collet H, Boiteau L, Taillades J, Vandenabeele-Trambouze O, Cottet H, Biron J-P, Plasson R, Mion L, Lagrille O, Martin H, Selsis F, Dobrijevic M (2002) Polym Int 51:661

    Article  Google Scholar 

  147. Commeyras A, Boiteau L, Vandenabeele-Trambouze O, Selsis F (2005) In: Gargaud M, Barbier B, Martin H, Reisse J (eds) Lectures in Astrobiology – Part II: From Prebiotic Chemistry to the Origins of Life on Earth (Advances in Astrobiology and Biogeophysics). Springer, Berlin Heidelberg New York, p 531

    Google Scholar 

  148. Navarro-Gonzalez R, Molina MJ, Molina LT (1998) Geophys Res Lett 25:3123

    Article  Google Scholar 

  149. Mather TA, Pyle DM, Allen AG (2004) Geology 32:905

    Article  Google Scholar 

  150. Plasson R, Biron J-P, Cottet H, Commeyras A, Taillades J (2002) J Chromatogr A 952:239

    Article  PubMed  Google Scholar 

  151. Liu R, Orgel LE (1997) Nature 389:52

    Article  PubMed  Google Scholar 

  152. Maurel M-C, Orgel LE (2000) Origins Life Evol Biosphere 30:423

    Article  Google Scholar 

  153. Leman L, Orgel LE, Ghadiri MR (2004) Science 306:283

    Article  PubMed  Google Scholar 

  154. Kortüm G, Vogel W, Andrussow K (1961) Dissociation constants of organic acids in aqueous solution. Butterworths, London

    Google Scholar 

  155. Di Sabato G, Jencks WP (1961) J Am Chem Soc 83:4393

    Article  Google Scholar 

  156. Mahler HR, Cordes EH (1966) Biological Chemistry, 1st edn. Harper & Row, New York

    Google Scholar 

  157. Holler E, Calvin M (1972) Biochemistry 11:3741

    Article  PubMed  Google Scholar 

  158. Stojanoski K, Zdravkovski Z (1993) J Chem Educ 70:134

    Google Scholar 

  159. Paecht-Horowitz M, Katchalsky A (1967) Biochim Biophys Acta 140:14

    Google Scholar 

  160. Lewinsohn R, Paecht-Horowitz M, Katchalsky A (1967) Biochim Biophys Acta 140:24

    Google Scholar 

  161. Wickramasinghe NSMD, Staves MP, Lacey JC (1991) Biochemistry 30:2768

    Article  PubMed  Google Scholar 

  162. Warden JT, McCullough JJ, Lemmon RM, Calvin M (1974) J Mol Evol 4:189

    Article  PubMed  Google Scholar 

  163. Holler E, Rainey P, Orme A, Bennett EL, Calvin M (1973) Biochemistry 12:1150

    Article  PubMed  Google Scholar 

  164. Berg P (2003) J Biol Chem 278:40417

    Article  PubMed  Google Scholar 

  165. Biron J-P, Pascal R (2004) J Am Chem Soc 126:9198

    Article  PubMed  Google Scholar 

  166. Kluger R, Li X, Loo RW (1996) Can J Chem 74:2395

    Google Scholar 

  167. Kluger R, Loo RW, Mazza V (1997) J Am Chem Soc 119:12089

    Article  Google Scholar 

  168. Yarus M (1999) Curr Opin Chem Biol 3:260

    Article  PubMed  Google Scholar 

  169. Illangasekare M, Yarus M (1997) J Mol Biol 268:631

    Article  PubMed  Google Scholar 

  170. Kumar RK, Yarus M (2001) Biochemistry 40:6998

    PubMed  Google Scholar 

  171. Tamura K, Schimmel P (2003) Proc Natl Acad Sci USA 100:8666

    Article  PubMed  Google Scholar 

  172. Tamura K, Schimmel P (2004) Science 305:1253

    Article  PubMed  Google Scholar 

  173. De Duve C (1992) In: Tran Thanh Van J, Tran Thanh Van K, Mounolou J-C, Schneider J, McKay C (eds) Frontiers of Life. Editions Frontières, Gif-sur-Yvette p 1

    Google Scholar 

  174. Lipmann F (1971) Science 173:875

    PubMed  Google Scholar 

  175. Di Giulio M (1996) Biosystems 39:159

    Article  PubMed  Google Scholar 

  176. Wieland T, Lambert R, Lang HU, Schramm G (1955) Liebigs Ann Chem 597:181

    Google Scholar 

  177. Weber AL, Orgel LE (1979) J Mol Evol 13:193

    Article  PubMed  Google Scholar 

  178. Wieland T, Bartmannn W (1956) Chem Ber 89:946

    Google Scholar 

  179. Wieland T, Euler KE (1958) Chem Ber 91:2305

    Google Scholar 

  180. Wieland T, Franz J, Pfleiderer G (1955) Chem Ber 88:641

    Google Scholar 

  181. Lazcano A, Miller SL (1996) Cell 85:793

    Article  PubMed  Google Scholar 

  182. Akabori S (1955) Kagaku 25:54

    Google Scholar 

  183. Akabori S (1959) In: Oparin AI, Braunstein AE, Pasinskii AG, Pavlovskaya TE (eds) Proceedings of the first international symposium: The origin of life on the Earth (Moscow, 1957). Pergamon Press, New York, p 189

    Google Scholar 

  184. Hanafusa H, Akabori S (1959) Bull Chem Soc Jpn 32:626

    Google Scholar 

  185. Ehler KW, Orgel LE (1976) Biochim Biophys Acta 434:233

    PubMed  Google Scholar 

  186. Wen K, Orgel LE (2001) Origins Life Evol Biosphere 31:241

    Article  Google Scholar 

  187. Blocher M, Hitz T, Luisi PL (2001) Helv Chim Acta 84:842

    Article  Google Scholar 

  188. Hitz T, Luisi PL (2003) Helv Chim Acta 86:1423

    Article  Google Scholar 

  189. Hitz T, Luisi PL (2000) Biopolymers 55:381

    Article  PubMed  Google Scholar 

  190. Hill AR, Bohler C, Orgel LE (1998) Origins Life Evol Biosphere 28:235

    Article  Google Scholar 

  191. Vaidyanathan R, Kalthod VG, Ngo DP, Manley JM, Lapekas SP (2004) J Org Chem 69:2565

    Article  PubMed  Google Scholar 

  192. Liu R, Orgel LE (1997) J Am Chem Soc 119:4791

    Article  PubMed  Google Scholar 

  193. Liu R, Orgel LE (1998) Origins Life Evol Biosphere 28:47

    Article  Google Scholar 

  194. Duvernay F, Chiavassa T, Borget F, Aycard J-P (2004) J Am Chem Soc 126:7772

    Article  PubMed  Google Scholar 

  195. Huber C, Wächtershäuser G (1998) Science 281:670

    Article  PubMed  Google Scholar 

  196. Plasson R, Bersini H, Commeyras A (2004) Proc Natl Acad Sci USA 101:16733

    Article  PubMed  Google Scholar 

  197. Collet H, Boiteau L, Taillades J, Commeyras A (1999) Tetrahedron Lett 40:3355

    Article  Google Scholar 

  198. Huber C, Eisenreich W, Hecht S, Wächtershäuser G (2003) Science 301:938

    Article  PubMed  Google Scholar 

  199. Pizzarello S, Weber AL (2004) Science 303:1151

    Article  PubMed  Google Scholar 

  200. Bloch K (1996) Chem Biol 3:405

    Article  PubMed  Google Scholar 

  201. Gao K, Orgel LE (2000) Origins Life Evol Biosphere 30:45

    Article  Google Scholar 

  202. Schimmel P, Henderson B (1994) Proc Natl Acad Sci USA 91:11283

    PubMed  Google Scholar 

  203. Tamura K, Alexander RW (2004) Cell Mol Life Sci 61:1317

    Article  PubMed  Google Scholar 

  204. Sievers A, Beringer M, Rodnina MV, Wolfenden R (2004) Proc Natl Acad Sci USA 101:7897

    Article  PubMed  Google Scholar 

  205. Di Giulio M (2003) Origins Life Evol Biosphere 33:479

    Article  Google Scholar 

  206. Terenzi S, Biaa E, Nguyen-Trung NQ, Strazewski P (2003) Angew Chem Int Ed 42:2909

    Article  Google Scholar 

  207. Orgel LE (1987) Cold Spring Harbor Symp Quant Biol 52:9

    PubMed  Google Scholar 

  208. Hartman H (1992) In: Tran Thanh Van J, Tran Thanh Van K, Mounolou J-C, Schneider J, McKay C (eds) Frontiers of Life. Editions Frontières, Gif-sur-Yvette p 163

    Google Scholar 

  209. Hollfelder F, Kirby AJ, Tawfik DS (2001) J Org Chem 66:5866

    Article  PubMed  Google Scholar 

  210. Lagnoux D, Delort E, Douat-Casassus C, Esposito A, Reymond J-L (2004) Chem Eur J 10:1215

    Article  Google Scholar 

  211. Clouet A, Darbre T, Reymond J-L (2004) Angew Chem Int Ed 43:4612

    Article  Google Scholar 

  212. Jarvo ER, Miller SJ (2002) Tetrahedron 58:2481

    Article  Google Scholar 

  213. Tang Z, Yang Z-H, Cun L-F, Gong L-Z, Mi A-Q, Jiang Y-Z (2004) Org Lett 6:2285

    Article  PubMed  Google Scholar 

  214. Wu Y-S, Shao W-Y, Zheng C-Q, Huang Z-L, Cai J, Deng Q-Y (2004) Helv Chim Acta 87:1377

    Article  Google Scholar 

  215. Kofoed J, Machuqueiro M, Reymond J-L, Darbre T (2004) Chem Commun:1540

    Google Scholar 

  216. Eberson L, Welinder H (1971) J Am Chem Soc 93:5821

    Article  Google Scholar 

  217. Johnson SL, Morrison DL (1972) J Am Chem Soc 94:1323

    Article  PubMed  Google Scholar 

  218. Caplow M (1968) J Am Chem Soc 90:6795

    Article  Google Scholar 

  219. Morrow JS, Keim P, Gurd FRN (1974) J Biol Chem 249:7484

    PubMed  Google Scholar 

  220. Davis AJ, O'Brien P, Nunn PB (1993) Bioorg Chem 21:309

    Article  Google Scholar 

  221. Chen J-G, Sandberg M, Weber SG (1993) J Am Chem Soc 115:7343

    Article  Google Scholar 

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Correspondence to Robert Pascal .

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Pascal, R., Boiteau, L., Commeyras, A. From the Prebiotic Synthesis of α-Amino Acids Towards a Primitive Translation Apparatus for the Synthesis of Peptides . In: Walde, P. (eds) Prebiotic Chemistry. Topics in Current Chemistry, vol 259. Springer, Berlin, Heidelberg. https://doi.org/10.1007/b136707

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