On the Conformation of Glycobilirubin

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Title:On the Conformation of Glycobilirubin
Creators:
Boiadjiev, Stefan E.
Lightner, David A.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 68, 5, pp. 1007-1019
Uncontrolled Keywords:Amino acids, Pyrroles, Conformation analysis, CD spectroscopy, Hydrogen bonding, Oligopyrroles, Porphyrins, Bilirubin, Glycine conjugate, NMR

Abstract

The first optically active glycine conjugate <strong>1</strong> of a bilirubin was prepared in several steps from (<i>S</i>)-β-methylxanthobilirubic acid glycine conjugate <strong>8</strong>. The latter was synthesized by reaction of benzyl glycinate tosylate with the mixed anhydride formed in the reaction of (<i>S</i>)-β-methylxanthobilirubic acid <strong>6</strong> with isobutyl chloroformate. Spectroscopic analysis of the circular dichroism spectra of <strong>1</strong> in various solvents, including aqueous buffer, indicate a conformational preference for the <strong><i>M</i></strong>-helical ridge-tile conformation, thus providing the first spectroscopic evidence on the conformation of glycobilirubins. <p>

Title:On the Conformation of Glycobilirubin
Creators:
Boiadjiev, Stefan E.
Lightner, David A.
Uncontrolled Keywords:Amino acids, Pyrroles, Conformation analysis, CD spectroscopy, Hydrogen bonding, Oligopyrroles, Porphyrins, Bilirubin, Glycine conjugate, NMR
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:68
Number:5
Page Range:pp. 1007-1019
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20031007UNSPECIFIED
ID Code:2099
Item Type:Article
Deposited On:06 Feb 2009 17:15
Last Modified:06 Feb 2009 16:15

Citation

Boiadjiev, Stefan E.; Lightner, David A. (2003) On the Conformation of Glycobilirubin. Collection of Czechoslovak Chemical Communications, 68 (5). pp. 1007-1019. ISSN 0010-0765

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