Crystal structure and conformation of a bilirubin ester

Monatshefte fur Chemie

Volumn 135, Issue 12, 2004, Pages 1503-1517

  Ghosh, Brahmananda ^a   Catalano, Vincent J ^a   Lightner, David A ^a  

^a UNIVERSITY OF NEVADA   (United States)

Author keywords

Bile pigments; Hydrogen bonding; Stereochemistry

Indexed keywords

BILIRUBIN; ESTER DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL PROCEDURES; CHEMICAL REACTION; CONFORMATION; CRYSTAL STRUCTURE; HYDROGEN BOND; MOLECULAR DYNAMICS; X RAY;

EID: 11244346677     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00706-004-0189-3     Document Type: Article

References (42)

1. McDonagh AF (1979) Bile Pigments: Bilatrienes and 5,15-Biladienes. In: Dolphin D (ed) The Porphyrins, vol 6. Academic Press, New York, p 293
2. Chowdhury JR, Wolkoff AW, Chowdhury NR, Arias IM (2001) Hereditary Jaundice and Disorders of Bilirubin Metabolism. In: Scriver CR, Beaudet AL, Sly WS, Valle D (eds) The Metabolic & Molecular Basis of Inherited Disease, vol II. McGraw-Hill, Inc, New York, pp 3063-3101
3. Falk H (1989) The Chemistry of Linear Oligopyrroles and Bile Pigments. Springer, Wien
4. Person RV, Peterson BR, Lightner DA (1994) J Am Chem Soc 116: 42
5. a) Bonnett R, Davies JE, Hursthouse MB, Sheldrick GM (1978) Proc R Soc London, Ser B 202: 249;
6. b) LeBas G, Allegret A, Mauguen Y, DeRango C, Bailly M (1980) Acta Crystallogr, Sect B B36: 3007;
7. c) Becker W, Sheldrick WS (1978) Acta Crystallogr, Sect B B34: 1298
8. Nogales DF, Ma JS, Lightner DA (1997) Tetrahedron 49: 2361
9. a) Huggins MT, Lightner DA (2000) J Org Chem 65: 6001;
10. b) Huggins MT, Lightner DA (2000) Tetrahedron 56: 1997;
11. c) Boiadjiev SE, Anstine DT, Lightner DA (1994) Tetrahedron: Asymm 5: 1945
12. Huggins MT, Lightner DA (2001) Monatsh Chem 132: 203
13. For a review of crystal structures of linear polypyrrolic compounds, see Sheldrick WS (1983) Israel J Chem 23: 155
14. Mugnoli A, Manitto D, Monti D (1983) Acta Crystallogr, Sect C 39: 287
15. Brown SP, Zhu XX, Saalwächter K, Spiess HW (2001) J Am Chem Soc 123: 4275
16. a) Kaplan D, Navon G (1983) Israel J Chem 23: 177;
17. b) Kaplan D, Navon G (1983) Org Magn Res 198;
18. c) Kaplan D, Navon G (1982) Biochem J 201: 605;
19. d) Navon G, Frank S, Kaplan D (1984) J Chem Soc Perkin Trans 2, 1145
20. a) Doerner T, Knipp B, Lightner DA (1997) Tetrahedron 53: 2697;
21. b) Nogales D, Lightner DA (1995) J Biol Chem 270: 73
22. Boiadjiev SE, Person RV, Puzicha G, Knobler C, Maverick E, Trueblood KN, Lightner DA (1992) J Am Chem Soc 114: 10123
23. a) Falk H, Müller N (1982) Monatsh Chem 112: 1325;
24. b) Falk H, Müller N (1983) Tetrahedron 39: 1875
25. a) Shelver WL, Rosenberg H, Shelver WH ( 1992) Intl J Quantum Chem 44: 141;
26. b) Alagona G, Ghio C, Agresti A, Pratesi R (1997) Intl J Quantum Chem 70: 395;
27. c) Alagona G, Ghio C, Monti S (2000) Phys Chem Chem Phys 2: 4884
28. Kar AK, Tipton AK, Lightner DA (1999) Monatsh Chem 130: 833
29. Tipton A, Lightner DA (2002) Monatsh Chem 133: 707
30. a) Xie M, Lightner DA (1993) Tetrahedron 49: 2185;
31. b) Xie M, Holmes DL, Lightner DA (1993) Tetrahedron 49: 9235
32. Brower JO, Huggins MT, Boiadjiev SE, Lightner DA (2000) Monatsh Chem 131: 1047
33. Bernett MJ, Tipton AK, Huggins MT, Reeder JH, Lightner DA (2000) Monatsh Chem 131: 239
34. a) Cullen DL, Black PS, Meyer EF, Lightner DA, Quistad GB, Pak C-S (1977) Tetrahedron 33: 477;
35. b) Cullen DL, Pepe G, Meyer Jr EF, Falk H, Grubmayr K (1979) J Chem Soc Perkin Trans 2, 999
36. Huggins MT, Lightner DA (2001) Monatsh Chem 132: 203
37. Kratky C, Jorde C, Falk H, Thirring K (1983) Tetrahedron 39: 1859
38. Sheldrick WS, Borkenstein A, Blacha-Puller M, Gossauer A (1977) Acta Crystallogr B33: 3625
39. Molecular mechanics and dynamics calculations employed to find the global energy minimum conformations of 1 were run on an SGI Octane workstation using vers. 6.9 of the Sybyl forcefield as described in Refs. [4, 14, 20]; for the Ball and Stick drawings were created from the atomic coordinates using Müller and Falk's "Ball and Stick" program for the Macintosh (http://www. orc.uni-Linz.ac.at/mueller/ball_and_stick.shtml).
40. Blessing R (1995) Acta Crystallogr A51: 33.
41. SAINT 6.1, Bruker Analytical X-Ray Systems, Madison, WI, USA
42. SHELXTL-Plus 5.10, Bruker Analytical X-Ray Systems, Madison, WI, USA