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Spectroscopy Letters
An International Journal for Rapid Communication
Volume 16, 1983 - Issue 10
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Original Articles

Intermolecular Hydrogen Bonding and Dimeric Structures in Bilirubin Esters from 1H-NMR Spectroscopy

D. A. Lightner Department of Chemistry, University of Nevada, Reno, Reno, Nevada, 89557
&
F. R. Trull Department of Chemistry, University of Nevada, Reno, Reno, Nevada, 89557
Pages 785-803 | Received 05 Jul 1983, Accepted 05 Aug 1983, Published online: 06 Dec 2006

Citations (33)

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Read on this site (4)

Yu-Ming Pu & DavidA. Lightner. (1991) On the Conformation of Bilirubin Dimethyl Ester from Circular Dichroism Spectroscopy. Spectroscopy Letters 24:7-8, pages 983-993.
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DavidA. Lightrier & Jing-Yi An. (1987) Circular Dichroism and Conformation of Bilirubin Bis N, N, N-Trimethyl α-Phenethylammonium Salts. Spectroscopy Letters 20:6-7, pages 491-508.
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DavidA. Lightner, Jin-Shi Ma & Xue-Xiong Wu. (1986) Intramolecular Hydrogen Bonding in Bilirubin Bis-Tetra-n-butyl Ammonium Salts as Determined by 1H-NMR Spectroscopy. Spectroscopy Letters 19:4, pages 311-320.
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D.A. Lightner & J.-S. Ma. (1984) Intramolecular Hydrogen Bonding in Bilirubin Monomethyl Esters Determined by 1H-NMR Spectroscopy. Spectroscopy Letters 17:4-5, pages 317-327.
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Articles from other publishers (29)

Hao Liu & Dongcheng Sun. (2021) Synthesis of self‐healing supramolecular waterborne polyurethane with quadruple hydrogen bonds via ureidotriazine. Journal of Applied Polymer Science 139:15, pages 51932.
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Simone Ghidinelli, Giovanna Longhi, Giuseppe Mazzeo, Sergio Abbate, Stefan E. Boiadjiev & David A. Lightner. (2018) On the aggregation of bilirubinoids in solution as evidenced by VCD and ECD spectroscopy and DFT calculations. Chirality 30:1, pages 19-28.
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Ranju Prasad Mandal, Gunjan Mandal, Sudeshna Sarkar, Arindam Bhattacharyya & Swati De. (2017) “Theranostic” role of bile salt-capped silver nanoparticles - gall stone/pigment stone disruption and anticancer activity. Journal of Photochemistry and Photobiology B: Biology 175, pages 269-281.
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Yu-Fang Shen, Ming-Rung Tsai, Shao-Chieh Chen, Yun-Shiuan Leung, Chien-Tai Hsieh, Yu-Shing Chen, Fu-Lien Huang, Rofeamor P. Obena, Medel Manuel L. Zulueta, Hsin-Yi Huang, Wen-Jeng Lee, Kuo-Chun Tang, Chun-Ta Kung, Min-Huey Chen, Dar-Bin Shieh, Yu-Ju Chen, Tzu-Ming Liu, Pi-Tai Chou & Chi-Kuang Sun. (2015) Imaging Endogenous Bilirubins with Two-Photon Fluorescence of Bilirubin Dimers. Analytical Chemistry 87:15, pages 7575-7582.
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Patricia D. MacLean, Erin E. Chapman, Sarah L. Dobrowolski, Alison Thompson & L. Ross C. Barclay. (2008) Pyrroles As Antioxidants: Solvent Effects and the Nature of the Attacking Radical on Antioxidant Activities and Mechanisms of Pyrroles, Dipyrrinones, and Bile Pigments. The Journal of Organic Chemistry 73:17, pages 6623-6635.
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Patricia D. MacLean, Emily C. Drake, L. Ross & C. Barclay. (2007) Bilirubin as an antioxidant in micelles and lipid bilayers: Its contribution to the total antioxidant capacity of human blood plasma. Free Radical Biology and Medicine 43:4, pages 600-609.
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Leonid L. Chepelev, Cory S. Beshara, Patricia D. MacLean, Gillian L. Hatfield, Amy A. Rand, Alison Thompson, James S. Wright & L. Ross C. Barclay. (2005) Polypyrroles as Antioxidants:  Kinetic Studies on Reactions of Bilirubin and Biliverdin Dimethyl Esters and Synthetic Model Compounds with Peroxyl Radicals in Solution. Chemical Calculations on Selected Typical Structures. The Journal of Organic Chemistry 71:1, pages 22-30.
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Stefan E. Boiadjiev & David A. Lightner. (2009) On the aggregation of bilirubins using vapor pressure osmometry. Journal of Heterocyclic Chemistry 37:4, pages 863-870.
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Ari K. Kar & David A. Lightner. (1998) Synthesis and properties of bilirubin analogs with conformation-perturbing C(10) tert-butyl and adamantyl groups. Tetrahedron 54:42, pages 12671-12690.
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Stefan E. Boiadjiev & David A. Lightner. (1997) Stereogenic competition in bilirubin conformational enantiomerism. Tetrahedron: Asymmetry 8:13, pages 2115-2129.
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Stefan E. Boiadjiev & David A. Lightner. (1996) Stereocontrol of bilirubin conformation. Tetrahedron: Asymmetry 7:5, pages 1309-1322.
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Thomas Thyrann & David A. Lightner. (1996) Synthesis and properties of a lipid bilirubin analog. Tetrahedron 52:2, pages 447-460.
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William P. Pfeiffer & David A. Lightner. (1994) Homorubin. A centrally homologated bilirubin. Tetrahedron Letters 35:52, pages 9673-9676.
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Ki-Oh Hwang, D.Timothy Anstine & David A. Lightner. (1994) Synthesis and properties of bilirubin analogs with N,N-methylene bridges. Tetrahedron 50:33, pages 9919-9932.
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Jian‐Jun Niu, Guang‐Jin Cheng & Shao‐Jun Dong. (2010) The electrooxidation behavior of bilirubin in DMF and DMF + H 2 O mixed solvent . Chinese Journal of Chemistry 12:1, pages 1-10.
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John Chiefari, Richard V. Person & David A. Lightner. (1992) Synthesis and conformation of a bilirubin analog with propionic acid side chains extended to undecanoic acid. Tetrahedron 48:29, pages 5969-5984.
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Francesc R. Trull & David A. Lightner. (1991) Synthesis of dipyrrinone esters using carbodiimide reagents. Tetrahedron 47:10-11, pages 1945-1956.
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J.K. Gawronski, T. Polonski & D.A. Lightner. (1990) Sulfoxides as chiral complexation agents. Conformational enantiomer resolution and induced circular dichroism of bilirubins. Tetrahedron 46:24, pages 8053-8066.
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Carme Anglada, Josep Claret, Joaquim Crusats, Joan-Anton Farrera, Josep M. Rib� & Francesc R. Trull. (1990) Reactivity of pyrrole pigments, part 13: Identification of the reaction product generated from bile pigments by the superoxide anionReaktivit�t von Pyrrolpigmenten, 13. Mitt.: Identifizierung der Reaktionsprodukte von Gallenpigmenten mit Superoxydanion. Monatshefte f�r Chemie Chemical Monthly 121:8-9, pages 653-663.
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D A Lighnter, W M Wijekoon & M H Zhang. (1988) Understanding bilirubin conformation and binding. Circular dichroism of human serum albumin complexes with bilirubin and its esters.. Journal of Biological Chemistry 263:32, pages 16669-16676.
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David A. Lightner, Jing-Yi An & Yu-Ming Pu. (1988) Circular dichroism of bilirubin-amine association complexes: Insights into bilirubin-albumin binding. Archives of Biochemistry and Biophysics 262:2, pages 543-559.
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David A. Lightner & Man-hua Zhang. (1988) Conformation of bilirubin amides from circular dichroism spectroscopy. Tetrahedron 44:15, pages 4679-4688.
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Francesc R. Trull, Roger W. Franklin & David A. Lightner. (2009) Total synthesis of symmetric bile pigments: Mesobilirubin‐IVα, mesobilirubin‐XIIIα and etiobilirubin‐IVγ. Journal of Heterocyclic Chemistry 24:6, pages 1573-1579.
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David A Lightner, Francesc R Trull & Man-Hua Zhang. (1987) Novel synthesis of bilirubin mono-esters. Tetrahedron Letters 28:10, pages 1047-1050.
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David A. Lightner & Jing-Yi An. (1987) Circular dichroism of bilirubin-amine heteroassociation complexes. Tetrahedron 43:19, pages 4287-4296.
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Pilar Castan, Ernest Giralt, Juan C. Perez, Josep M. Ribo, Nuria Siscart & Francesc R. Trull. (1987) Polymer bound pyrrole compounds- II. Tetrahedron 43:11, pages 2593-2608.
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Norbert Müller. (2005) Complete Assignments of the 13 C NMR Spectra of Bilirubin‐IXα and its Dimethyl Ester . Magnetic Resonance in Chemistry 23:8, pages 688-689.
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J.‐S. Ma & D. A. Lightner. (2009) Facile preparation of symmetric bilirubins IIIα and XIIIα from IXα. Journal of Heterocyclic Chemistry 21:4, pages 1005-1008.
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D.A. Lightner, T.C. Adams & J.S. Ma. (1984) Bilirubin mono and bis-dimethylamides. synthesis, spectroscopy and solution structures. Tetrahedron 40:21, pages 4253-4260.
Crossref

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