Linked Life Data

11735518

Source:http://linkedlifedata.com/resource/pubmed/id/11735518

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
25
pubmed:dateCreated
2001-12-12
pubmed:abstractText
(4Z)-8-(5-Carboxypentyl)-9-butyl-2,3-diethyl-dipyrrin-1-one (1), a new analogue of xanthobilirubic acid, (4Z)-8-(carboxyethyl)-2,7,9-dimethyl-3-ethyl-dipyrrin-1-one, was synthesized in four steps from the known 2,3-diethyl-dipyrrin-1-one. Whereas xanthobilirubic acid (which is a model for one-half of bilirubin, the yellow pigment of jaundice) and its homologues with hexanoic and longer acid chains at C-8 engage only in intermolecular hydrogen bonding, 1 is found to engage in intramolecular hydrogen bonding. In CDCl(3) solution, dipyrrinone 1 adopts an anti-Z conformation, and its hexanoic acid COOH is hydrogen-bonded to the lactam H-N-C=O and to the pyrrole C(7)-H but not to the pyrrole NH. The latter constitutes an example of a hydrogen bond of the type C-H...O=C, weak and detected typically in crystals. Dipyrrinone 1 is found by vapor pressure osmometry to be monomeric in CHCl(3), but its methyl ester (2) tends toward being dimeric, like that of methyl xanthobilirubinate, which is dimeric.
pubmed:grant
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Dec
pubmed:issn
0022-3263
pubmed:author
pubmed:issnType
Print
pubmed:day
14
pubmed:volume
66
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
8402-10
pubmed:dateRevised
2007-11-14
pubmed:meshHeading
pubmed:year
2001
pubmed:articleTitle
A C-H...O=C hydrogen bond? Intramolecular hydrogen bonding in a novel semirubin.
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