| pubmed-article:2039452 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:2039452 | lifeskim:mentions | umls-concept:C0002074 | lld:lifeskim |
| pubmed-article:2039452 | lifeskim:mentions | umls-concept:C0017857 | lld:lifeskim |
| pubmed-article:2039452 | lifeskim:mentions | umls-concept:C1414968 | lld:lifeskim |
| pubmed-article:2039452 | lifeskim:mentions | umls-concept:C2700116 | lld:lifeskim |
| pubmed-article:2039452 | pubmed:dateCreated | 1991-7-3 | lld:pubmed |
| pubmed-article:2039452 | pubmed:abstractText | Two new alkylating reagents, chloro- and bromo-acetylphosphonate, were found to be very effective thiol-blocking reagents. The pH-dependence of the reaction of BAP with 2,4-dinitrothiophenol (25 degrees C, I 0.5) shows a tailing bell-shaped curve (with a plateau at high pH) characteristic of two ionizing groups: the thiol group (pKa 3.2) and the phosphonate group (pKa2 4.6). The rate constant for the reaction of the monoanionic inhibitor with dinitrothiophenolate (k2 = 7 M-1.s-1) is 120 times larger than that of the dianionic species. The haloacetylphosphonates were found to be irreversible inhibitors of glyceraldehyde-3-phosphate dehydrogenase from a variety of sources. They react with the active-site thiol group (Cys-149) and are half-site reagents with yeast glyceraldehyde-3-phosphate dehydrogenase. Thus, when two of the identical four subunits are modified the enzyme is catalytically inactive. The effects of pH (7-10), 2H2O and NAD+ on the reaction with the yeast enzyme were examined in detail. NAD+ enhances the alkylation rates. The second-order rate constant does not show a simple sigmoidal dependence on pH but rather a tailing bell-shaped curve (pKa 7.0 and 8.4) qualitatively similar to that obtained with dinitrothiophenol. There is no significant solvent isotope effect on the limiting rate constants and a normal isotope effect on the two pKa values. The results are consistent with the more reactive enzyme species containing a thiolate and an acidic group that may either donate a proton to the dianionic haloacetylphosphonate or orient the inhibitor. | lld:pubmed |
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| pubmed-article:2039452 | pubmed:language | eng | lld:pubmed |
| pubmed-article:2039452 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:2039452 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:2039452 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:2039452 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:2039452 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
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| pubmed-article:2039452 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:2039452 | pubmed:month | May | lld:pubmed |
| pubmed-article:2039452 | pubmed:issn | 0264-6021 | lld:pubmed |
| pubmed-article:2039452 | pubmed:author | pubmed-author:ByersL DLD | lld:pubmed |
| pubmed-article:2039452 | pubmed:author | pubmed-author:MAY TYT | lld:pubmed |
| pubmed-article:2039452 | pubmed:author | pubmed-author:BoggaramJJ | lld:pubmed |
| pubmed-article:2039452 | pubmed:issnType | Print | lld:pubmed |
| pubmed-article:2039452 | pubmed:day | 1 | lld:pubmed |
| pubmed-article:2039452 | pubmed:volume | 275 ( Pt 3) | lld:pubmed |
| pubmed-article:2039452 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:2039452 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:2039452 | pubmed:pagination | 767-73 | lld:pubmed |
| pubmed-article:2039452 | pubmed:dateRevised | 2009-11-18 | lld:pubmed |
| pubmed-article:2039452 | pubmed:meshHeading | pubmed-meshheading:2039452-... | lld:pubmed |
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| pubmed-article:2039452 | pubmed:meshHeading | pubmed-meshheading:2039452-... | lld:pubmed |
| pubmed-article:2039452 | pubmed:year | 1991 | lld:pubmed |
| pubmed-article:2039452 | pubmed:articleTitle | Alkylation of glyceraldehyde-3-phosphate dehydrogenase with haloacetylphosphonates. An unusual pH-dependence. | lld:pubmed |
| pubmed-article:2039452 | pubmed:affiliation | Department of Chemistry, Tulane University, New Orleans, LA 70118. | lld:pubmed |
| pubmed-article:2039452 | pubmed:publicationType | Journal Article | lld:pubmed |
| pubmed-article:2039452 | pubmed:publicationType | Comparative Study | lld:pubmed |
| pubmed-article:2039452 | pubmed:publicationType | Research Support, U.S. Gov't, P.H.S. | lld:pubmed |
