Linked Life Data

20535768

Source:http://linkedlifedata.com/resource/pubmed/id/20535768

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
7
pubmed:dateCreated
2010-6-16
pubmed:abstractText
Solution NMR methods were used for the structural characterization of the acetoxyendiyne E/Z configuration of the marine natural products peyssonenynes A and B and their synthetic analogs derived from palmitic acid. The scarcity of protons in the proximity of the olefin precluded the determination of the double bond geometry using (1)H NMR methods that rely on proton-proton scalar couplings or experiments such as NOESY or ROESY. Long range (1)H-(13)C heteronuclear scalar couplings, (n)J(CH), measured with the 2D excitation sculptured indirect detection experiment (EXSIDE) proved useful and highly reliable for the analysis of the enol acetate geometry. In addition, it was found that the chemical shift of some carbon atoms in the proximity of the olefin was also sensitive to the double bond configuration of these molecules providing an even simpler way to determine their geometry. This protocol showed its robustness by similar analysis of simpler silyl-protected acetoxyenynes derived from fatty acids. These NMR experimental results and stereochemical predictions were rationalized by DFT calculations.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Jul
pubmed:issn
1097-458X
pubmed:author
pubmed:copyrightInfo
Copyright (c) 2010 John Wiley & Sons, Ltd.
pubmed:issnType
Electronic
pubmed:volume
48
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
543-9
pubmed:dateRevised
2011-11-17
pubmed:meshHeading
pubmed:year
2010
pubmed:articleTitle
Determination of the geometry of acetoxyendiynes and acetoxyenynes by NMR heteronuclear (13)C-(1)H scalar couplings and (13)C NMR chemical shifts. Structural assignment of the oxylipin natural products peyssonenynes A and B.
pubmed:affiliation
Universidade de Vigo, Facultad de Química, Department of Organic Chemistry, As Lagoas-Marcosende, 36315 Vigo, Spain.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't