29790-14-5Relevant academic research and scientific papers
Syntheses of Biliverdins (Bilin-1,19-diones from a,c-Biladienes and b-Bilenes
Smith, Kevin M.,Kishore, Dharma
, p. 888 - 890 (1982)
Treatment of readily accessible 1,19-bis(t-butoxycarbonyl)-a,c-biladienes or b-bilenes with bromine in trifluoroacetic acid affords excellent yields of biliverdins (bilin-1,19-diones).
An efficient synthesis of symmetric bilindiones. Mesobilirubin-XIIIα and analogs with varying alkanoic acid chain lengths
Shrout,Puzicha,Lightner
, p. 328 - 332 (1992)
An inexpensive gram-scale, three-step procedure is described to convert methyl xanthobilirubinate and it alkanoic acid ester analogs (methyl 5-[(3-ethyl-1,5-dihydro-4-methyl-5-oxo-2H-pyrrol-2- ylidene)methyl]-1,4-dimethylpyrrol-3-ethanoate, -propanoate, -butanoate, -pentanoate, -hexanoate) into mesobilirubin-XIIIα and analogs in >90% yield at each step.
1,2-bis-Dipyrrinon-9-yl-ethene - a Novel b-homo-Verdin Chromophore: the Reaction of 9-Methyl-10H-dipyrrin-1-ones with Bromine
Chen, Q.-Q.,Ma, J.-S.,Wang, C.-Q.,Liu, Y.-Y.,Yan, F.,et al.
, p. 983 - 992 (1995)
Upon treatment of 9-methyl-10H-dipyrrin-1-ones with bromine in dichloromethane, red bile pigment derivatives were obtained in moderate yields.They were structurally assigned as 1,2-bis-dipyrrinon-9-yl-ethenes, which are examples of the hitherto unknown b-homo-verdins.In addition, the corresponding meso-biliverdins-XIIIα could be isolated from the reaction mixture.The mechanistic aspects of the reaction are discussed. - Keywords: 1,2-bis-Dipyrrinon-9-yl-ethene; b-homo-Verdin; Mesobiliverdin-XIIIα
Intramolecular hydrogen bonding and its influence on conformation. Circular dichroism of chiral bilirubin analogs
Boiadjiev, Stefan E.,Lightner, David A.
, p. 2535 - 2550 (2007/10/03)
Enantiopure synthetic bilirubin analogs with variously modified (e.g. alkyl for natural propionic acid or ester) C(8) and C(12) side chains and with but a single chiral center in either or both exhibited exciton coupled circular dichroism (CD) spectra. The CD intensity is greater when the stereogenic center is in a propionic acid side chain than in an alkyl side chain.
A Novel 16,24-Dehydrobiladiene-ab System: The Reaction of Xanthobilirubic acid methyl ester with Bromine
Ma, J.-S.,Chen, Q.-Q.,Wang, C.-Q.,Liu, Y.-Y.,Yan, F.,et al.
, p. 201 - 210 (2007/10/02)
On treating xanthobilirubic acid methyl ester with bromine in methanol, a red bile pigment, which was assigned the hitherto unknown 16,24-dehydrobiladiene-ab constitution, is obtained in 20percent yield.In addition, the corresponding mesobiliverdin-XIIIα, mesobilirubin-XIIIα, 14-formyl-tripyrrinone, and two diastereomeric 15,16-dimethoxybiladienes-ab could be isolated from the reaction mixture.The mechanistic aspects of this reaction are discussed. - Keywords. 16,24-Dehydrobiladiene-ab; Biladiene-ab; Xanthobilirubic acid methyl ester; Mesobilirubin-XIIIα; Mesobiliverdin-XIIIα; 14-Formyl-tripyrrinone; 15,16-Dimethoxy-biladienes-ab.
Synthesis of Unsymmetric Bile Pigments: Mesobilirubin-VIIIα, 17-Desvinyl-17-ethyl-bilirubin-VIIIα and 12-Despropionic Acid-12-ethyl-mesobilirubin-XIIIα
Trull, Francesc R.,Lightner, David A.
, p. 1227 - 1230 (2007/10/02)
The unnatural bile pigments 17-desvinyl-17-ethylbilirubin-VIIIα, mesobilirubin-VIIIα and 12-despropionic acid-12-ethyl mesobilirubin-XIIIα were synthesized via (1) "reverse scrambling" of bilirubin-XIIIα or mesobilirubin-IXα with mesobilirubin-IVα or etiobilirubin-IVγ or (2) following coupling of xanthobilirubic acid methyl ester with ψ-xanthobilirubic acid methyl ester, or coupling of xanthobilirubic acid methyl ester with kryptopyrromethenone.
BILE PIGMENT STUDIES-VI. SYNTHESES OF MODEL SYSTEMS
Smith, Kevin M.,Kishore, Dharma
, p. 1841 - 1848 (2007/10/02)
The synthesis of various mammalian and algal bile pigment models from monopyrroles and by ring cleavage of intact metalloporphyrins and metallochlorins is discussed.A previously reported synthesis of etiobiliverdin IVγ (6) from the self-condensation of a
