Linked Life Data

3517331

Source:http://linkedlifedata.com/resource/pubmed/id/3517331

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
5
pubmed:dateCreated
1986-6-20
pubmed:abstractText
A stereospecific synthesis of thiorphan [N-[2(RS)-(mercaptomethyl)-1-oxo-3-phenylpropyl]glycine] and retro-thiorphan [3-[[1(RS)-(mercaptomethyl)-2-phenylethyl]amino]-3-oxopropanoic acid], two highly potent inhibitors of enkephalinase, a neutral endopeptidase involved in enkephalin metabolism, is reported. Due to a rapid isomerization process, derivatives of retro-thiorphan, which contains a 2-substituted malonyl moiety, cannot be separated by classical methods. However, a separation of the diastereoisomeric mixtures of these retro-thiorphan derivatives was achieved by HPLC. The absolute configuration of each isomer was determined by using an NMR configurational correlation. The inhibitory potency of the various inhibitors indicates that, in the thiorphan series, the affinity for enkephalinase is independent of the stereochemistry of the 2-(mercaptomethyl)-1-oxo-3-phenylpropyl moiety. In contrast, in the retro-thiorphan series a 100-fold difference in the inhibitory activity of the two enantiomers is observed. This indicates that there are large differences in the conformational behavior of the two series of inhibitors at the active site of the enzyme.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
May
pubmed:issn
0022-2623
pubmed:author
pubmed:issnType
Print
pubmed:volume
29
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
751-7
pubmed:dateRevised
2010-11-18
pubmed:meshHeading
pubmed:year
1986
pubmed:articleTitle
1H NMR configurational correlation for retro-inverso dipeptides: application to the determination of the absolute configuration of "enkephalinase" inhibitors. Relationships between stereochemistry and enzyme recognition.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't