Synthesis of a 10-Oxo-bilirubin: effects of the Oxo group on conformation, transhepatic transport, and glucuronidation

…, DA Lightner, W Norona, AF McDonagh

Index: Chen, Qingqi; Huggins, Michael T.; Lightner, David A.; Norona, Wilma; McDonagh, Antony F. Journal of the American Chemical Society, 1999 , vol. 121, # 40 p. 9253 - 9264

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Citation Number: 49

Abstract

Bilirubin, the yellow pigment of jaundice, is a linear tetrapyrrole with a methylene group at its center, C (10), a position of crucial importance to its conformation and metabolism. The presence of the central methylene group allows the bilirubin to fold into an intramolecularly hydrogen-bonded conformation. This paper describes the first synthesis of a bilirubin analogue with an oxo group at C (10). The change from CH2 to CO, from sp3 to sp2, is ...