Oxidative acylation using thioacids

Nature

Volumn 389, Issue 6646, 1997, Pages 52-54

  Liu, Rihe ^a   Orgel, Leslie E ^a  

^a SALK INSTITUTE FOR BIOLOGICAL STUDIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CARBOXYLIC ACID; LEUCINE; OXIDIZING AGENT; PHENYLALANINE; PHOSPHATE; THIOACID;

ACYLATION; ARTICLE; ATMOSPHERE; CHEMICAL REACTION; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS;

NASA DISCIPLINE EXOBIOLOGY; NON-NASA CENTER;

ACYLATION; BIOGENESIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FERRICYANIDES; NITRILES; OXIDATION-REDUCTION; PHENYLALANINE; PHOSPHORIC ACID ESTERS; SULFHYDRYL COMPOUNDS;

EID: 0030963854     PISSN: 00280836     EISSN: None     Source Type: Journal    
DOI: 10.1038/37944     Document Type: Article

References (18)

1. Hulshof, J. & Ponnamperuma, C. Prebiotic condensation reactions in an aqueous medium: a review of condensing agents. Orig. Life 7, 197-224 (1976).
2. Ferris, J. P. in Cold Spring Harbor Symposia on Quantitative Biology 29-35 (Cold Spring Harbor Lab Press, Cold Spring Harbor, NX 1987).
3. Hawker, J. R. J. & Oro, J. Cyanamide mediated syntheses of peptides containing histidine and hydrophobic amino acids. J. Mol. Evol. 17, 285-294 (1981).
4. Weber, A. L. & Orgel, L. E. The formation of peptides from glycine thioesters. J. Mol. Evol. 13, 193-202 (1979).
5. Weber, A. L. Formation of pyrophosphate, tripolyphosphate, and phosphorylimidazole with the thioester, n,s-diacetyl-cysteamine, as the condensing agent. J. Mol. Evol. 18, 24-29 (1981).
6. de Duve, C. Blueprint for A Cell: The Nature and Origin of Life (Patterson Publishers, Carolina Biological Supply Co., Burlington, NC, 1991).
7. Keller, M., Blöchl, E., Wächtershäuser, G. & Stetter, K. Ö. Formation of amide bonds without a condensation agent and implications for origin of life. Nature 368, 836-838 (1994).
8. Wieland, T. in The Roots of Modern Biochemistry: Fritz Lipmann's Squiggle and its Consequences (eds Kleinkauf, H., von Dohren, H. & Lothar, J.) 213-221 (de Gruyter, Berlin, 1988).
9. Sheehan, J. C. & Johnson, D. A. The synthesis and reactions of N-acylthiol amino acids. J. Am. Chem. Soc. 74, 4726-4727 (1952).
10. Dawson, P. E., Muir, T. W., Clark-Lewis, I. & Kent, S. B. H. Synthesis of proteins by native chemical ligation. Science 266, 776-779 (1994).
11. Liu, C., Rao, C. & Tam, J. P. Acyl disulfide-mediated intramolecular acylation for orthogonal coupling between unprotected peptide segments. Mechanism and application. Tetrahedr. Lett. 37, 933-936 (1996).
12. Smith, P. A. S. The Chemistry of Open-chain Organic Nitrogen Compounds 165-166 (Benjamin, New York, 1965).
13. Rosenthal, D. & Taylor, T. I. A study of the mechanism and kinetics of the thioacetamide hydrolysis reaction. J. Am. Chem. Soc. 79, 2684-2690 (1957).
14. Butler, E. A., Peters, D. G. & Swift, E. H. Hydrolysis reactions of thioacetamide in aqueous solutions. Anal. Chem. 30, 1379-1383 (1958).
15. Cefola, M., Peter, S. S., Gentile, P. S. & Celiano, R. A. V. Rate of hydrolysis of thiolacetic acid in basic solution. Talanta 9, 537-542 (1962).
16. 2+ - significance for banded iron formations. Nature 303, 163-164 (1983).
17. Whittet, D. C. B. Is extraterrestrial organic matter relevant to the origin of life on earth? Orig. Life Evol. Biosphere 27, 249-262 (1997).
18. Huber, C. St Wächtershäuser, G. Activated acetic acid by carbon fixation on (Fe, Ni)S under primordial conditions. Science 276, 245-247 (1997).