Dihydroxyacetone phosphate, DHAP, in the crystalline state: monomeric and dimeric forms

Carbohydrate Research

Volumn 345, Issue 4, 2010, Pages 512-529

  Ślepokura, Katarzyna ^a   Lis, Tadeusz ^a  

^a UNIVERSITY OF WROC AW   (Poland)

Author keywords

DHAP; DHAP synthesis; DHAP dimer; Dihydroxyacetone phosphate; Stable DHAP salts; X ray crystal structure

Indexed keywords

[CARBONYL; AQUEOUS SOLUTIONS; AXIAL POSITIONS; CALCIUM CATIONS; CHAIR CONFORMATIONS; CRYSTALLINE SALTS; CRYSTALLINE STATE; DHAP SYNTHESIS; DIHYDROXYACETONE; DIHYDROXYACETONE PHOSPHATE; DIOXANE RINGS; EQUATORIAL POSITIONS; HYDROXYL GROUPS; IN-PLANE; MONOANIONIC FORMS; MONOANIONS; OXYGEN ATOM; PHOSPHATE OXYGEN; ROOM TEMPERATURE; STRUCTURAL FEATURE; TRANS ISOMERS; X RAY CRYSTAL STRUCTURES;

ATOMS; CALCIUM; CALCIUM ALLOYS; CALCIUM CHLORIDE; CHELATION; COMPLEXATION; COORDINATION REACTIONS; CRYSTAL ATOMIC STRUCTURE; CRYSTALLINE MATERIALS; CRYSTALLIZATION; DYES; ESTERS; ETHERS; HYDRATES; OXYGEN; SALTS;

X RAY CRYSTALLOGRAPHY;

AMMONIA; CALCIUM CHLORIDE; CATION; CRYSTALLIN; DIHYDROXYACETONE; DIHYDROXYACETONE PHOSPHATE; DIOXANE; HYDROXYL GROUP; MONOMER;

AQUEOUS SOLUTION; ARTICLE; ATOM; CHELATION; COMPLEX FORMATION; CONFORMATION; CRYSTAL STRUCTURE; CRYSTALLIZATION; ISOMER; PRIORITY JOURNAL; ROOM TEMPERATURE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BROMIDES; CALCIUM CHLORIDE; CALCIUM COMPOUNDS; CHELATING AGENTS; CRYSTALLIZATION; CRYSTALLOGRAPHY, X-RAY; DIHYDROXYACETONE; DIHYDROXYACETONE PHOSPHATE; DIMERIZATION; DIOXANES; ESTERS; IONS; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXYGEN; SOLUTIONS; WATER;

EID: 75149112679     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2009.12.008     Document Type: Article

References (50)

1. Ślepokura K., and Lis T. Carbohydr. Res. 339 (2004) 1995-2007
2. Ślepokura K., and Lis T. Acta Crystallogr., Sect. C 60 (2004) o315-o317
3. Ślepokura K., and Lis T. Carbohydr. Res. 341 (2006) 507-524
4. Ślepokura K. Carbohydr. Res. 343 (2008) 113-131
5. Ślepokura K., and Lis T. Acta Crystallogr., Sect. C 64 (2008) m127-m133
6. Stryer L. Biochemistry. 3rd ed. (1988), W.H. Freeman and Company, New York
7. Nomenclature Committee of the International Union of Biochemistry and Molecular Biology (NC-IUBMB) Eur. J. Biochem. 1999, 264, 610-650.
8. Cambridge Structural Database (CSD):. Allen F.H. Acta Crystallogr., Sect. B 58 (2002) 380-388
9. Espelt L., Parella T., Bujons J., Solans C., Joglar J., Delgado A., and Clapés P. Chem. Eur. J. 9 (2003) 4887-4899
10. Fessner W.-D., and Helaine V. Curr. Opin. Biotechnol. 12 (2001) 574-586
11. Koeller K.M., and Wong C.-H. Chem. Rev. 100 (2000) 4465-4494
12. Machajewski T.D., and Wong C.-H. Angew. Chem., Int. Ed. 39 (2000) 1352-1375
13. Gijsen H.J.M., Qiao L., Fitz W., and Wong C.-H. Chem. Rev. 96 (1996) 443-474
14. Wong C.-H., Halcomb R.L., Ichikawa Y., and Kajimoto T. Angew. Chem., Int. Ed. Engl. 34 (1995) 412-432
15. Webb M.R., Standring D.N., and Knowles J.R. Biochemistry 16 (1977) 2738-2741
16. Reynolds S.J., Yates D.W., and Pogson C.I. Biochem. J. 122 (1971) 285-297
17. Gray G.R. Biochemistry 10 (1971) 4705-4711
18. Gray G.R., and Barker R. Biochemistry 9 (1970) 2454-2462
19. Davis L. Bioorg. Chem. 2 (1973) 197-201
20. Strain H.H., and Dore W.H. J. Am. Chem. Soc. 56 (1934) 2649-2650
21. Yaylayan V.A., Harty-Majors S., and Ismail A.A. Carbohydr. Res. 318 (1999) 20-25
22. Yaylayan V.A., and Ismail A.A. Carbohydr. Res. 276 (1995) 253
23. Richard J.P. J. Am. Chem. Soc. 106 (1984) 4926-4936
24. Leloir L.F., and Cardini C.E. Characterization of Phosphorus Compounds by Acid Lability. In: Colowick S.P., and Kaplan N.O. (Eds). Methods in Enzymology Vol. 3 (1957), Academic Press, New York 840-849 and references cited therein
25. Berman H.M., Westbrook J., Feng Z., Gilliland G., Bhat T.N., Weissig H., Shindyalov I.N., and Bourne P.E. Nucleic Acids Res. 28 (2000) 235-242. http://www.rcsb.org/pdb/ http://www.rcsb.org/pdb/
26. Pompiliano D.L., Peyman A., and Knowles J.R. Biochemistry 29 (1990) 3186-3194
27. Saadat D., and Harrison D.H.T. Biochemistry 39 (2000) 2950-2960
28. Kursula I., and Wierenga R.K. J. Biol. Chem. 278 (2003) 9544-9551
29. Zhang X., Harrison D.H.T., and Cui Q. J. Am. Chem. Soc. 124 (2002) 14871-14878
30. Jogl G., Rozovsky S., McDermott A.E., and Tong L. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 50-55
31. Sigel H., and Kapinos L.E. Coord. Chem. Rev. 200-202 (2000) 563-594
32. Liang G., Chen D., Bastian M., and Sigel H. J. Am. Chem. Soc. 114 (1992) 7780-7785
33. Wong C.-H., and Whitesides G.M. J. Org. Chem. 48 (1983) 3199-3205
34. Ballou C.E., and Fischer H.O.L. J. Am. Chem. Soc. 78 (1956) 1659-1661
35. Ballou C.E. Dihydroxyacetone Phosphate. In: Lardy H.A. (Ed). Biochemical Preparations Vol. 7 (1960), John Wiley & Sons, New York 45-50
36. Valentin M.-L., and Bolte J. Bull. Soc. Chim. Fr. 132 (1995) 1167-1171
37. Charmantray F., Blidi L.E., Gefflaut T., Hecquet L., Bolte J., and Lemaire M. J. Org. Chem. 69 (2004) 9310-9312
38. Meyer O., Rohmer M., and Grosdemange-Billiard C. Tetrahedron Lett. 45 (2004) 7921-7923
39. André C., Demuynck C., Gefflaut T., Guérard C., Hecquet L., Lemaire M., and Bolte J. J. Mol. Catal. B: Enzym. 5 (1998) 113-118
40. Gefflaut T., Lemaire M., Valentin M.-L., and Bolte J. J. Org. Chem. 62 (1997) 5920-5922
41. Effenberger F., and Straub A. Tetrahedron Lett. 28 (1987) 1641-1644
42. Pederson R.L., Esker J., and Wong C.-H. Tetrahedron 47 (1991) 2643-2648
43. Jung S.-H., Jeong J.-H., Miller P., and Wong C.-H. J. Org. Chem. 59 (1994) 7182-7184
44. Ferroni E.L., DiTella V., Ghanayem N., Jeske R., Jodlowski C., O'Connel M., Styrsky J., Svoboda R., Venkataraman A., and Winkler B.M. J. Org. Chem. 64 (1999) 4943-4945
45. Doxsee K.M., Ferguson C.M., Wash P.L., and Saulsbery R.L. J. Org. Chem. 58 (1993) 7557-7561
46. Einspahr H., and Bugg C.E. Acta Crystallogr., Sect. B 37 (1981) 1044-1052
47. Kuma km4ccd software: CrysAlisCCD and CrysAlisRED, ver. 1.171 Oxford Diffraction Poland, 1995-2003.
48. Sheldrick G.M. Acta Crystallogr., Sect. A 64 (2008) 112-122
49. XP-Interactive Molecular Graphics, v. 5.1-Bruker Analytical X-ray Systems, 1998.
50. Spek, A. L. platon-A Multipurpose Crystallographic Tool. Utrecht University, Utrecht, The Netherlands, 2003; Spek, A. L., J. Appl. Crystallogr. 2003, 36, 7-13.