Linked Life Data

10987933

Source:http://linkedlifedata.com/resource/pubmed/id/10987933

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
19
pubmed:dateCreated
2000-11-7
pubmed:abstractText
(4Z)-9-(5-Carboxypentyl)-2,3,7,8-tetramethyl-(10H)-dipyrrin- 1-one (1, semirubin), a new dipyrrinone model for one-half of bilirubin, the yellow-orange neurotoxic pigment of jaundice, was synthesized following Friedel-Crafts acylation of 2,3,7, 8-tetramethyl-(10H)-dipyrrin-1-one (5) with the half-ester acid chloride of adipic acid. Unlike other dipyrrinone models for bilirubin, such as the xanthobilirubic acids, which engage only in intermolecular hydrogen bonding, 1 is unique in having been designed and found to engage in intramolecular hydrogen bonding, between the carboxylic acid and the dipyrrinone lactam and pyrrole. This important conformation-determining structural characteristic, shared by 1 and bilirubin, renders them less polar than their methyl esters and leaves them monomeric in nonpolar solvents, where their esters are dimeric. The corresponding 10-oxo analogue (3) of 1 serves as a model for 10-oxo-bilirubin, a presumed bilirubin metabolite in alternate pathways for bilirubin excretion. Like 1, 3 is found to engage in intramolecular hydrogen bonding. Unlike the methyl ester of 1, the ethyl ester of 3 is not intermolecularly hydrogen bonded in nonpolar solvents.
pubmed:grant
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Sep
pubmed:issn
0022-3263
pubmed:author
pubmed:issnType
Print
pubmed:day
22
pubmed:volume
65
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
6001-8
pubmed:dateRevised
2007-11-14
pubmed:meshHeading
pubmed:year
2000
pubmed:articleTitle
Semirubin. A novel dipyrrinone strapped by intramolecular hydrogen bonds.
pubmed:affiliation
Department of Chemistry, University of Nevada, Reno, Nevada 89557-0020, USA.
pubmed:publicationType
Journal Article, Research Support, U.S. Gov't, P.H.S., Research Support, Non-U.S. Gov't