Linked Life Data

2493815

Source:http://linkedlifedata.com/resource/pubmed/id/2493815

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
3
pubmed:dateCreated
1989-5-8
pubmed:abstractText
At physiological pH values, the rearrangement of adrenochrome leads, besides adrenolutin, to a major dimeric compound consisting of an adrenolutin moiety covalently linked to the angular 9-position of adrenochrome. When the reaction is carried out in air, the initially generated adrenolutin undergoes autoxidation to give 5,6-dihydroxy-1-methyl-isatin (DHMIs), which is smoothly oxidized to the 4,4'-dimer. Under an oxygen-depleted atmosphere, formation of these latter compounds is prevented, and the rearrangement of adrenochrome leads mainly to the adrenochrome dimer (about 50% yield) along with adrenolutin and 5,6-dihydroxy-1-methylindole (DHMI) in about 10% yield each. The product distribution is markedly dependent on the concentration of the aminochrome undergoing rearrangement, the nature of the buffer system used, and the pH of the medium. Heavy metal ions of common occurrence in biological systems, such as Cu2+, Zn2+, Co2+, significantly direct the reaction course towards the formation of adrenolutin, while Fe2+ and other cations with low redox potentials induce the almost exclusive formation of DHMI.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Mar
pubmed:issn
0006-3002
pubmed:author
pubmed:issnType
Print
pubmed:day
24
pubmed:volume
990
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
297-302
pubmed:dateRevised
2008-11-21
pubmed:meshHeading
pubmed:year
1989
pubmed:articleTitle
A new look at the rearrangement of adrenochrome under biomimetic conditions.
pubmed:affiliation
Stazione Zoologica, Villa Communale, Università di Napoli, Italy.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't