Prebiotic carbohydrate synthesis: Zinc-proline catalyzes direct aqueous aldol reactions of α-hydroxy aldehydes and ketones

Organic and Biomolecular Chemistry

Volumn 3, Issue 10, 2005, Pages 1850-1855

  Kofoed, Jacob ^a   Reymond, Jean Louis ^a   Darbre, Tamis ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYSIS; KETONES; PRECIPITATION (CHEMICAL); RNA; SYNTHESIS (CHEMICAL); ZINC;

ALDOL REACTIONS; ALDOLIZATION; GLYCOALDEHYDE; ROOM TEMPERATURE (RT);

CARBOHYDRATES;

3-HYDROXYBUTANAL; ALDEHYDE; ALDOL; CARBOHYDRATE; KETONE; PROLINE; ZINC;

ACETYLATION; ARTICLE; BIOSYNTHESIS; CATALYSIS; CHEMISTRY; GAS CHROMATOGRAPHY;

ACETYLATION; ALDEHYDES; CARBOHYDRATES; CATALYSIS; CHROMATOGRAPHY, GAS; KETONES; PROLINE; ZINC;

EID: 19944415654     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b501512j     Document Type: Article

References (48)

1. For reviews of prebiotic chemistry see: (a) J. D. Sutherland and J. N. Whitfield, Tetrahedron, 1997, 53, 11493-11527;
2. (b) R. A. Hughes, M. P. Robertson, A. D. Ellington and M. Levy, Curr. Opin. Chem. Biol., 2004, 8, 629-633;
3. (c) S. A. Benner, A. Ricardo and M. A. Carrigan, Curr. Opin. Chem. Biol., 2004, 8, 672-689.
4. (a) W. Gilbert, Nature, 1986, 319, 618;
5. (b) P. A. Sharp, Cell, 1985, 42, 397-400;
6. (c) for a review on the construction of an "RNA-world" see: D. P. Bartel and P. J. Unrau, Trends. Cell. Biol., 1999, 12, M9-M13.
7. J. R. Lorsch and J. W. Szostak, Nature, 1994, 371, 31-36.
8. M. Illangasekare, Science, 1995, 267, 643-647.
9. B. L. Zhang and T. R. Cech, Nature, 1997, 390, 96-100.
10. T. M. Tarasow, Nature, 1997, 389, 54-57.
11. S. L. Miller and H. C. Urey, J. Am. Chem. Soc., 2000, 77, 2351.
12. J. M. Hollis, F. J. Lovas and P. R. Jewell, Astrophys. J. Lett., 2000, 540, L107-L110.
13. Comets and the Origin and Evolution of Life, ed. P. J. Thomas, C. P. McKay and C. F. Chyba, Springer-Verlag, New York, 1997, pp. 3-19, J. Oró and A. Lazcano; pp. 29-62, A. Delsemme; for a recent update see:;
14. S. Pizzrello, Origins Life Evol. Biosphere, 2004, 34, 25-34.
15. (a) A. Butlerow, Liebigs Ann. Chem., 1861, 120, 295;
16. (b) E. H. Ruckert, E. Pfeil and G. Scharf, Chem. Ber., 1965, 98, 2558;
17. (c) G. Harsch, H. Bauer and W. Voelter, Liebigs Ann. Chem., 1984, 623;
18. (d) N. W. Gabel and C. Ponnamperuma, Nature, 1967, 216, 453;
19. (e) C. Reid and L. E. Orgel, Nature, 1967, 216, 455;
20. (f) R. F. Socha and A. H. Weiss, J. Catal., 1981, 67, 207.
21. (a) R. Larralde, M. P. Robertson and S. L. Miller, Proc. Natl. Acad. Sci. USA, 1995, 92, 8158-8160;
22. (b) R. Shapiro, Origins Life Evol. Biosphere, 1988, 18, 71-85.
23. G. Springsteen and G. F. Joyce, J. Am. Chem. Soc., 2004, 126, 9578-9583.
24. G. Zubay, Origins Life Evol. Biosphere, 1998, 28, 13-26.
25. A. L. Weber, J. Mol. Evol., 1992, 35, 1-6.
26. A. Ricardo, M. A. Carrigan, A. N. Olcott and S. A. Benner, Science, 2004, 303, 196.
27. (a) D. Müller, S. Pitsch, A. Kittaka, E. Wagner, C. E. Wintner and A. Eschenmoser, Helv. Chim. Acta, 1990, 73, 1410;
28. (b) R. Krishnamurthy, S. Pitsch and G. Arrhenius, Origins Life Evol. Biosphere, 1999, 29, 139-152.
29. (a) A. L. Weber, Origins Life Evol. Biosphere, 2001, 31, 71-86;
30. (b) S. Pizzarello and A. L. Weber, Science, 2004, 303, 1151.
31. For a review of chemoenzymatic synthesis of carbohydrates see: H. J. M. Gijsen, L. Qiao, W. Fitz and C.-H. Wong, Chem. Rev., 1996, 443-473.
32. 2O 10 : 1):;
33. A. Córdova, W. Notz and C. F. Barbas III, Chem. Commun., 2002, 24, 3024.
34. (a) For a recent proline catalyzed synthesis of protected sugars see: A. B. Northrup, I. K. Mangion, F. Hettche and D. W C. Macmillan, Angew. Chem., Int. Ed., 2004, 43, 2152;
35. (b) A. B. Northrup and D. W C. Macmillan, Science, 2004, 305, 1752-1755.
36. For amine-catalyzed aldol reactions in water see: T. J. Dickerson and K. D. Janda, J. Am. Chem. Soc., 2002, 124, 3220;
37. Y. Chen and J.-L. Reymond, J. Org. Chem., 1995, 60, 6970.
38. (a) J. Kofoed, J. Nielsen and J.-L. Reymond, Bioorg. Med. Chem. Lett., 2003, 15, 2445-2447;
39. (b) Z. Tang, Z.-H. Yang, L.-F. Cun, L.-Z. Gong, A.-Q. Mi and Y.-Z. Jiang, Org. Lett., 2004, 6, 2285-2287;
40. (c) H. J. Martin and B. M. List, SYNLETT, 2003, 12, 1901-1902.
41. T. Darbre and M. Machuqueiro, Chem. Commun., 2003, 1090.
42. J. Kofoed, M. Machuqueiro, J.-L. Reymond and T. Darbre, Chem. Commun., 2004, 1540-1541.
43. G. Schultz and M. Dreyer, J. Mol. Biol., 1996, 259, 458.
44. C.-H. Ng, H.-K. Fun, S.-B. Teo, S.-G. Teoh and K. Chinnakali, Acta Crystallogr., Sect. C, 1995, 51, 244.
45. J. S. Sawardeker, J. H. Sloneker and A. Jeanes, Anal. Chem., 1965, 12, 1602-1604.
46. 2, talose, and galactose were formed in larger amount.
47. (a) W. R. Jones and P. C. Dedon, J. Am. Chem. Soc., 1999, 121, 9231-9232;
48. (b) a potential prebiotic pathway from glycolaldehyde to glycolaldehyde phosphate using amidotriphosphate has been reported by R. Krishnamurthy, G. Arrhenius and A. Eschenmoser, Origins Life Evol. Biosphere, 1999, 29, 333-354.