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α-Amino acid behaves differently from β- or γ-amino acids as treated by trimetaphosphate

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Summary.

The condensation reactions of sodium trimetaphosphate with single amino acids, namely glycine, L-alanine, β-alanine and γ-aminobutyric acid or pairs of these amino acids were reinvestigated by electrospray ion-trap mass spectrometry and high performance liquid chromatography. It was found when mixtures were treated by sodium trimetaphosphate only in the presence of α-amino acid dipeptides were formed. Without addition of α-amino acids, the β-amino acid or γ-aminobutyric acid could not form peptide either by themselves or with their mixtures under the same conditions. From the data it is concluded that phosphate might select α-amino acids to produce the peptides being important precursors for the origin of life.

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References

  • JY Bao HW Ai H Fu YY Jiang YF Zhao (2005) ArticleTitlePeptide sequencing through N-terminal phosphorylation and electrospray ionization mass spectrometry J Mass Spectrom 40 772–776 Occurrence Handle15880623 Occurrence Handle10.1002/jms.850 Occurrence Handle1:CAS:528:DC%2BD2MXmtVyjsrc%3D

    Article  PubMed  CAS  Google Scholar 

  • K Biemann HA Scoble (1987) ArticleTitleCharacterization by tandem mass spectrometry of structural modifications in proteins Science 237 992–998 Occurrence Handle3303336 Occurrence Handle10.1126/science.3303336 Occurrence Handle1:CAS:528:DyaL2sXmtlagsLc%3D

    Article  PubMed  CAS  Google Scholar 

  • P Chaimbault K Petritis C Elfakir M Dreux (2000) ArticleTitleIon-pair chromatography on a porus graphitic carbon stationary phase for the analysis of twenty underivatized protein amino acids J Chromatagr A 870 245–254 Occurrence Handle10.1016/S0021-9673(99)00863-8 Occurrence Handle1:CAS:528:DC%2BD3cXpsFKguw%3D%3D

    Article  CAS  Google Scholar 

  • J Chen Y Chen P Gong Y Jiang YM Li YF Zhao (2002) ArticleTitleA novel phosphoryl derivatization method for peptide sequencing by electrospray ionization spectrometry Rapid Comm Mass Spectrom 16 325–329

    Google Scholar 

  • CM Cheng C Fan R Wan CY Tong ZW Miao J Chen YF Zhao (2002) ArticleTitlePhosphorylation of adenosine with trimetaphosphate under simulated prebiotic conditions Orig Life Evol B 32 219–224 Occurrence Handle10.1023/A:1016513114799 Occurrence Handle1:CAS:528:DC%2BD38XlsV2gu7Y%3D

    Article  CAS  Google Scholar 

  • N Chung R Lohrmann LE Orgel J Rabinowitz (1971) ArticleTitleThe mechanism of the trimetaphosphate-induced peptide synthesis Tetrahedron 27 1205–1210 Occurrence Handle10.1016/S0040-4020(01)90868-3 Occurrence Handle1:CAS:528:DyaE3MXktVKhu7g%3D

    Article  CAS  Google Scholar 

  • MM Cordero JJ Houser C Wesdemiotis (1993) ArticleTitleThe neutral products formed during backbone fragmentations of protonated peptides in tandem mass spectrometry Anal Chem 65 1594–1601 Occurrence Handle8328675 Occurrence Handle10.1021/ac00059a019 Occurrence Handle1:CAS:528:DyaK3sXisFGgsbo%3D

    Article  PubMed  CAS  Google Scholar 

  • RM De Graaf AW Schwartz (2005) ArticleTitleThermal synthesis of nucleosides H-phosphonates under mild conditions Orig Life Evol B 35 1–10 Occurrence Handle10.1007/s11084-005-0093-9 Occurrence Handle1:CAS:528:DC%2BD2MXjvVyiurw%3D

    Article  CAS  Google Scholar 

  • AG Harrison IG Csizmadia TH Tang YP Tu (2000) ArticleTitleReaction competition in the fragmentation of protonated dipeptides J Mass Spectrom 35 683–688 Occurrence Handle10862119 Occurrence Handle10.1002/1096-9888(200006)35:6<683::AID-JMS994>3.0.CO;2-D Occurrence Handle1:CAS:528:DC%2BD3cXkt1aisL8%3D

    Article  PubMed  CAS  Google Scholar 

  • A Hill LE Ogel (2002) ArticleTitleTrimetaphosphate-induced addition of aspartic acid to oligo (glutamic acid)s Helv Chim Acta 85 4244–4254 Occurrence Handle10.1002/hlca.200290009 Occurrence Handle1:CAS:528:DC%2BD3sXmvFylsw%3D%3D

    Article  CAS  Google Scholar 

  • H Inoue Y Baba T Furukawa Y Maeda M Tsuhako (1993) ArticleTitleFormation of dipeptide in the reaction of amino acids with cyclo-triphosphate Chem Pharm Bull 41 1895–1899 Occurrence Handle1:CAS:528:DyaK2cXjt1Ciu7w%3D

    CAS  Google Scholar 

  • B Paizs M Schnolzer U Warnken S Shhai AG Harrison (2004) ArticleTitleCleavage of the amide bond of the protonated dipeptides Phys Chem Chem Phys 6 2691–2699 Occurrence Handle10.1039/b315597h Occurrence Handle1:CAS:528:DC%2BD2cXktVWrsb8%3D

    Article  CAS  Google Scholar 

  • IA Papayannopoulos (1995) ArticleTitleThe interpretation of collision-induced dissociation tandem mass spectra of peptides Mass Spectrom Rev 14 49–73 Occurrence Handle10.1002/mas.1280140104 Occurrence Handle1:CAS:528:DyaK28Xis1ShsQ%3D%3D

    Article  CAS  Google Scholar 

  • MD Person A Sevestre P Chaimbault L Perrot F Duchiron C Elfakir (2004) ArticleTitleCharacterization of low-molecular weight peptides in champagne wine by liquid chromatography/tandem mass spectrometry Anal Chim Acta 520 149–158 Occurrence Handle10.1016/j.aca.2004.03.094

    Article  Google Scholar 

  • K Petritis S Brussaux S Guenu C Elfakir M Dreux (2002) ArticleTitleIon-pair reversed-phase liquid chromatography-electrospray mass spectrometry for the analysis of underivatized small peptides J Chromatogr A 957 173–185 Occurrence Handle12113341 Occurrence Handle10.1016/S0021-9673(02)00372-2 Occurrence Handle1:CAS:528:DC%2BD38XjvVSmsb4%3D

    Article  PubMed  CAS  Google Scholar 

  • K Petritis P Chaimbault C Elfakir M Dreux (1999) ArticleTitleDetermination of 20 underivatized proteinic amino acids by ion-pairing chromatography and pneumatically assisted electrospray mass spectrometry J Chromatagr A 855 191–202 Occurrence Handle10.1016/S0021-9673(99)00685-8

    Article  Google Scholar 

  • J Rabinowitz (1970) ArticleTitlePeptide and amide bond formation in aqueous solutions of cyclic or linear polyphosphates as a possible prebiotic process Helv Chim Acta 53 1350–1355 Occurrence Handle5471413 Occurrence Handle10.1002/hlca.19700530614 Occurrence Handle1:CAS:528:DyaE3cXltFKgsb8%3D

    Article  PubMed  CAS  Google Scholar 

  • J Rabinowitz J Flores R Krebsbach G Rogers (1969) ArticleTitlePeptide formation in the presence of linear or cyclic polyphosphates Nature 224 795–796 Occurrence Handle4188388 Occurrence Handle10.1038/224795a0 Occurrence Handle1:CAS:528:DyaE3cXltFSiug%3D%3D

    Article  PubMed  CAS  Google Scholar 

  • M Tsuhako M Fujimoto S Ohashi H Nariai I Motooka (1984) ArticleTitlePhosphorylation of nucleosides with sodium cyclo-triphosphate Bull Chem Soc Jpn 57 3274–3280 Occurrence Handle10.1246/bcsj.57.3274 Occurrence Handle1:CAS:528:DyaL2MXhs1Ojtbo%3D

    Article  CAS  Google Scholar 

  • M Tsuhako A Nakajima T Miyajima S Ohashi H Nariai I Motooka (1985) ArticleTitleThe reaction of cyclo-triphosphate with L-α- or β-alanine Bull Chem Soc Jpn 41 3092–3098 Occurrence Handle10.1246/bcsj.58.3092

    Article  Google Scholar 

  • Y Yamagata K Inomata (1997) ArticleTitleCondensation of glycylglycine to oligoglycines with trimetaphosphate in aqueous solution Orig Life Evol B 27 339–344 Occurrence Handle10.1023/A:1006529421813 Occurrence Handle1:CAS:528:DyaK2sXltlKgur4%3D

    Article  CAS  Google Scholar 

  • Y Yamagata H Watanabe M Saitoh T Namba (1991) ArticleTitleVolcanic production of polyphosphates and its relevance to prebiotic evolution Nature 352 516–519 Occurrence Handle11536483 Occurrence Handle10.1038/352516a0 Occurrence Handle1:CAS:528:DyaK38XovFWk

    Article  PubMed  CAS  Google Scholar 

  • DC Yang L Fan YG Zhong (2003) ArticleTitleSynthesis of protected RGD tripeptide Chin J Org Chem 23 493–498 Occurrence Handle1:CAS:528:DC%2BD3sXksVymu7g%3D

    CAS  Google Scholar 

  • GJ Zhou Z Liu TJ Wang PX Xu G Tang Y Ye YF Zhao (2005) ArticleTitleElectrospray ionization mass spectrometry study on dipeptide 4-chlorobutyl ester produced from refluxing of amino acids with phosphoryl chloride in tetrahydrofuran J Mass Spectrom 40 1382–1386 Occurrence Handle16220467 Occurrence Handle10.1002/jms.918 Occurrence Handle1:CAS:528:DC%2BD2MXht1Sgu7bE

    Article  PubMed  CAS  Google Scholar 

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Authors and Affiliations

  1. The Key Laboratory for Chemical Biology of Fujian Province, Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, China

    X. Gao, Y. Liu, P. X. Xu, Y. M. Cai & Y. F. Zhao

  2. Department of Medicine, Medical college, Xiamen University, Xiamen, China

    Y. F. Zhao

  3. The Key Laboratory for Bioorganic Phosphorus Chemistry, Ministry of Education, Department of Chemistry, School of Life Sciences and Engineering, Tsinghua University, Beijing, China

    Y. F. Zhao

Authors
  1. X. Gao
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  2. Y. Liu
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  3. P. X. Xu
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  4. Y. M. Cai
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  5. Y. F. Zhao
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Corresponding author

Correspondence to P. X. Xu.

Additional information

Authors’ address: Dr. Pengxiang Xu, The Key Laboratory for Chemical Biology of Fujian Province, Department of Chemistry, Xiamen University, Xiamen 361005, China

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Gao, X., Liu, Y., Xu, P. et al. α-Amino acid behaves differently from β- or γ-amino acids as treated by trimetaphosphate. Amino Acids 34, 47–53 (2008). https://doi.org/10.1007/s00726-007-0599-8

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  • DOI: https://doi.org/10.1007/s00726-007-0599-8

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