Syntheses, crystal structures, and conformations of 10,10-spiro-bilirubins

Monatshefte fur Chemie

Volumn 135, Issue 10, 2004, Pages 1305-1317

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

^a UNIVERSITY OF NEVADA   (United States)

Author keywords

Hydrogen bonding; Linear tetrapyrroles; Stereochemistry

Indexed keywords

BILIRUBIN DERIVATIVE;

ARTICLE; CALCULATION; CONFORMATION; CRYSTAL STRUCTURE; HYDROGEN BOND; LIPOPHILICITY; MOLECULAR DYNAMICS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 7044271005     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00706-004-0216-4     Document Type: Article

References (39)

1. Falk H (1989) The Chemistry of Linear Oligopyrroles and Bile Pigments. Springer, Wien
2. McDonagh AF (1979) Bile Pigments: Bilatrienes and 5,15-Biladienes. In: Dolphin D (ed) The Porphyrins, vol 6. Academic Press, New York, p 293
3. Chowdhury JR, Wolkoff AW, Chowdhury NR, Arias IM (1979) Hereditary Jaundice and Disorders of Bilirubin Metabolism. In: Scriver CR, Beaudet AL, Sly WS, Valle D (eds) The Metabolic and Molecular Basis of Inherited Disease, vol II. McGraw-Hill, New York, pp 2161-2208
4. Person RV, Peterson BR, Lightner DA (1994) J Am Chem Soc 116: 42
5. Huggins MT, Lightner DA (2001) Monatsh Chem 132: 203
6. Nogales DF, Ma JS, Lightner DA (1993) Tetrahedron 49: 2361
7. Boiadjiev SE, Anstine DT, Lightner DA (1994) Tetrahedron Asymm 5: 1945
8. Huggins MT, Lightner DA (2001) Tetrahedron 57: 2279
9. a) Bonnett R, Davies JE, Hursthouse MB, Sheldrick GM (1978) Proc R Soc London Ser B 202: 249;
10. b) LeBas G, Allegret A, Mauguen Y, DeRango C, Bailly M (1980) Acta Crystallogr Sect B B36: 3007;
11. c) Becker W, Sheldrick WS (1978) Acta Crystallogr Sect B B34: 1298
12. Brown SP, Zhu XX, Saalwächter K, Spiess HW (2001) J Am Chem Soc 123: 4275
13. a) Kaplan D, Navon G (1983) Israel J Chem 23: 177;
14. b) Kaplan D, Navon G (1983) Org Magn Res 198;
15. c) Kaplan D, Navon G (1982) Biochem J 201: 605;
16. d) Navon G, Frank S, Kaplan D (1984) J Chem Soc Perkin Trans 2, 1145
17. a) Doerner T, Knipp B, Lightner DA (1997) Tetrahedron 53: 2697;
18. b) Nogales D, Lightner DA (1995) J Biol Chem 270: 73
19. Boiadjiev SE, Person RV, Puzicha G, Knobler C, Maverick E, Trueblood KN, Lightner DA (1992) J Am Chem Soc 114: 10123
20. For a review of crystal structures of linear polypyrrolic compounds, see Sheldrick WS (1983) Israel J Chem 23: 155
21. Mugnoli A, Manitto D, Monti D (1983) Acta Crystallogr Sect C 39: 287
22. Kar AK, Tipton AK, Lightner DA (1999) Monatsh Chem 130: 833
23. Tipton A, Lightner DA (2002) Monatsh Chem 133: 707
24. a) Xie M, Lightner DA (1993) Tetrahedron 49: 2185;
25. b) Xie M, Holmes DL, Lightner DA (1993) Tetrahedron 49: 9235
26. a) Taylor EC, Chiang C-S (1977) Synthesis 467;
27. b) Bakthayachalam V, Lin LG, Chenan XM, Czarnik AW (1987) Carbohydrate Research 170: 124
28. a) Huggins MT, Lightner DA (2000) J Org Chem 65: 6001;
29. b) Huggins MT, Lightner DA (2000) Tetrahedron 56: 1797
30. a) Brower JO, Lightner DA, McDonagh AF (2000) Tetrahedron 56: 7869;
31. b) Boiadjiev SE, Lightner DA (1999) Tetrahedron Asymm 10: 2535
32. a) Trull FR, Shrout DP, Lightner DA (1992) Tetrahedron 48: 8189;
33. b) Gawroński JK, Polonski T, Lightner DA (1990) Tetrahedron 46: 8053
34. Kratky C, Jorde C, Falk H, Thirring K (1983) Tetrahedron 39: 1859
35. Sheldrick WS, Borkenstein A, Blacha-Puller M, Gaossauer A (1977) Acta Crystallogr B33: 3625
36. Molecular mechanics and dynamics calculations employed to find the global energy minimum conformations of 1, 2, and 4 were run on an SGI Octane workstation using vers. 6.9 of the Sybyl forcefield as described in Ref. [4]
37. Blessing R (1995) Acta Crystallogr A51: 33
38. SAINT V6.1, Bruker Analytical X-ray Systems. Madison, WI, USA
39. SHELXTL-Plus V5.10, Bruker Analytical X-ray Systems. Madison, WI, USA