rdf:type |
|
lifeskim:mentions |
umls-concept:C0022646,
umls-concept:C0031603,
umls-concept:C0034417,
umls-concept:C0037494,
umls-concept:C0043309,
umls-concept:C0178523,
umls-concept:C0205344,
umls-concept:C0205369,
umls-concept:C0302923,
umls-concept:C0449830,
umls-concept:C0936012,
umls-concept:C1611588,
umls-concept:C1999216,
umls-concept:C2827597
|
pubmed:issue |
9
|
pubmed:dateCreated |
1995-6-7
|
pubmed:abstractText |
Racemic [fluoro(hydroxyphenylphosphinyl)methyl]phosphonic acid (1) and its individual enantiomers [(+), 98% ee; (-), 67% ee] were previously shown to inhibit Na(+)-gradient-dependent Na(+)-phosphate cotransport across renal brush border membrane, without measurable stereospecificity. Resolution of 1 was effected by fractional recrystallization of its (-)-quinine salts. The more levorotatory, diquinine product 2, corresponding to (+)-1, has now been analyzed by X-ray crystallography and found to be composed of the S enantiomer of 1. This result confirms the absence of stereochemical preference in inhibition of the cotransporter by the enantiomers of 1 and provides the first absolute configuration assignment of an asymmetrical alpha-halomethylene pyrophosphate analogue.
|
pubmed:grant |
|
pubmed:language |
eng
|
pubmed:journal |
|
pubmed:citationSubset |
IM
|
pubmed:chemical |
|
pubmed:status |
MEDLINE
|
pubmed:month |
Apr
|
pubmed:issn |
0022-2623
|
pubmed:author |
|
pubmed:issnType |
Print
|
pubmed:day |
28
|
pubmed:volume |
38
|
pubmed:owner |
NLM
|
pubmed:authorsComplete |
Y
|
pubmed:pagination |
1575-8
|
pubmed:dateRevised |
2007-11-14
|
pubmed:meshHeading |
pubmed-meshheading:7739016-Carrier Proteins,
pubmed-meshheading:7739016-Crystallography, X-Ray,
pubmed-meshheading:7739016-Diphosphonates,
pubmed-meshheading:7739016-Kidney,
pubmed-meshheading:7739016-Magnetic Resonance Spectroscopy,
pubmed-meshheading:7739016-Microvilli,
pubmed-meshheading:7739016-Molecular Conformation,
pubmed-meshheading:7739016-Quinine,
pubmed-meshheading:7739016-Salts,
pubmed-meshheading:7739016-Sodium,
pubmed-meshheading:7739016-Sodium-Phosphate Cotransporter Proteins,
pubmed-meshheading:7739016-Symporters
|
pubmed:year |
1995
|
pubmed:articleTitle |
Absolute configuration of (+)-[fluoro(hydroxyphenylphosphinyl)methyl]-phosphonic acid, a specific inhibitor of Na(+)-gradient-dependent Na(+)-phosphate cotransport across renal brush border membrane, by X-ray crystallographic analysis of its (-)-quinine salt.
|
pubmed:affiliation |
Department of Chemistry, University of Southern California, Los Angeles 90089-0744, USA.
|
pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, P.H.S.,
Research Support, U.S. Gov't, Non-P.H.S.
|