FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2094144896> ?p ?o ?g. }

• W2094144896 abstract "Lecithin:cholesterol acyltransferase (LCAT), the enzyme that esterifies cholesterol in blood, also esterifies other steroids at the 3beta-hydroxyl. These steroids, like cholesterol, are delta5-3beta-hydroxysteroids, such as pregnenolone and dehydroepiandrosterone. One unusual LCAT substrate is the estrogen, estradiol, which is esterified at the 17beta-hydroxyl. The esterification of estradiol by LCAT has been reported to produce a powerful antioxidant that protects low density lipoprotein (LDL) from oxidation. We investigated the substrate specificity of LCAT, comparing the esterification of four different steroids (estradiol, estriol, testosterone, and 5-androstene-3beta, 17beta-diol) by human LCAT in blood and by acyl-coenzyme A:acyltransferase in tissue (placenta and fat). Estradiol was esterified only at the D ring 17beta-hydroxyl group in both blood and tissue. In contrast, although testosterone has a D ring structure identical to that of estradiol, and it was esterified at the 17beta-hydroxyl by acyl-coenzyme A:acyltransferase in tissue, it was not esterified by LCAT. When 5-androstenediol was the substrate in the tissues, both the 3beta- and 17beta-esters were synthesized, but the major product was the 17beta-ester. Conversely, although 5-androstenediol was an excellent substrate for LCAT, only the 3beta-hydroxyl was esterified. No 17beta-ester was formed. The comparison of the esterification of estriol by acyl-coenzyme A:acyltransferase and LCAT was also surprising. In the tissues, estriol is esterified at both D ring hydroxyls, and both are esterified about equally. Although estriol is an extremely polar estrogen, it is esterified by LCAT, albeit at a very slow rate. Although again both D ring hydroxyls were esterified, the LCAT esterification site was mainly at the 17beta-hydroxyl. Esterification of estriol at the 17beta-hydroxyl in preference to the 16alpha-hydroxyl is especially striking, because the 17beta-hydroxyl group is sterically shielded by the C-18 methyl group, making esterification at this position energetically much more difficult. Furthermore, these studies demonstrate that esterification of the 17beta-hydroxyl group by LCAT is unique to estrogens. It suggests that this unusual regiospecific esterification of C-17 of the estrogens underlies a distinct stereochemical requirement for the powerful antioxidant action that has reported for the estradiol esters formed by LCAT." @default.
• W2094144896 created "2016-06-24" @default.
• W2094144896 creator A5010674766 @default.
• W2094144896 creator A5032444656 @default.
• W2094144896 creator A5036854356 @default.
• W2094144896 creator A5088842069 @default.
• W2094144896 date "1999-07-01" @default.
• W2094144896 modified "2023-10-18" @default.
• W2094144896 title "Regiospecific Esterification of Estrogens by Lecithin:Cholesterol Acyltransferase1" @default.
• W2094144896 cites W1501652397 @default.
• W2094144896 cites W1523155597 @default.
• W2094144896 cites W1538428170 @default.
• W2094144896 cites W1565659772 @default.
• W2094144896 cites W1972055919 @default.
• W2094144896 cites W1972209675 @default.
• W2094144896 cites W1977333419 @default.
• W2094144896 cites W1977508911 @default.
• W2094144896 cites W1983197987 @default.
• W2094144896 cites W1983981695 @default.
• W2094144896 cites W1985552418 @default.
• W2094144896 cites W1988172735 @default.
• W2094144896 cites W1993053801 @default.
• W2094144896 cites W1993318146 @default.
• W2094144896 cites W1996704795 @default.
• W2094144896 cites W1998025448 @default.
• W2094144896 cites W2001306586 @default.
• W2094144896 cites W2006032290 @default.
• W2094144896 cites W2007459994 @default.
• W2094144896 cites W2011247197 @default.
• W2094144896 cites W2018312028 @default.
• W2094144896 cites W2018392898 @default.
• W2094144896 cites W2022495947 @default.
• W2094144896 cites W2038319337 @default.
• W2094144896 cites W2044081276 @default.
• W2094144896 cites W2046098819 @default.
• W2094144896 cites W2050559583 @default.
• W2094144896 cites W2054850987 @default.
• W2094144896 cites W2057092725 @default.
• W2094144896 cites W2062671014 @default.
• W2094144896 cites W2073289405 @default.
• W2094144896 cites W2075916880 @default.
• W2094144896 cites W2079538027 @default.
• W2094144896 cites W2082218696 @default.
• W2094144896 cites W2083461853 @default.
• W2094144896 cites W2092161964 @default.
• W2094144896 cites W2094437404 @default.
• W2094144896 cites W2094588318 @default.
• W2094144896 cites W2098646953 @default.
• W2094144896 cites W2135730400 @default.
• W2094144896 cites W2139046695 @default.
• W2094144896 cites W2151459643 @default.
• W2094144896 doi "https://doi.org/10.1210/jcem.84.7.5755" @default.
• W2094144896 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/10404824" @default.
• W2094144896 hasPublicationYear "1999" @default.
• W2094144896 type Work @default.
• W2094144896 sameAs 2094144896 @default.
• W2094144896 citedByCount "13" @default.
• W2094144896 countsByYear W20941448962012 @default.
• W2094144896 countsByYear W20941448962013 @default.
• W2094144896 countsByYear W20941448962014 @default.
• W2094144896 countsByYear W20941448962022 @default.
• W2094144896 crossrefType "journal-article" @default.
• W2094144896 hasAuthorship W2094144896A5010674766 @default.
• W2094144896 hasAuthorship W2094144896A5032444656 @default.
• W2094144896 hasAuthorship W2094144896A5036854356 @default.
• W2094144896 hasAuthorship W2094144896A5088842069 @default.
• W2094144896 hasBestOaLocation W20941448961 @default.
• W2094144896 hasConcept C126322002 @default.
• W2094144896 hasConcept C134018914 @default.
• W2094144896 hasConcept C181199279 @default.
• W2094144896 hasConcept C185592680 @default.
• W2094144896 hasConcept C2775970874 @default.
• W2094144896 hasConcept C2776448209 @default.
• W2094144896 hasConcept C2776992908 @default.
• W2094144896 hasConcept C2777164284 @default.
• W2094144896 hasConcept C2777335581 @default.
• W2094144896 hasConcept C2777911890 @default.
• W2094144896 hasConcept C2778163477 @default.
• W2094144896 hasConcept C2778656385 @default.
• W2094144896 hasConcept C2779279991 @default.
• W2094144896 hasConcept C2779283022 @default.
• W2094144896 hasConcept C2779564620 @default.
• W2094144896 hasConcept C2780072125 @default.
• W2094144896 hasConcept C37002583 @default.
• W2094144896 hasConcept C55493867 @default.
• W2094144896 hasConcept C71315377 @default.
• W2094144896 hasConcept C71924100 @default.
• W2094144896 hasConcept C86803240 @default.
• W2094144896 hasConceptScore W2094144896C126322002 @default.
• W2094144896 hasConceptScore W2094144896C134018914 @default.
• W2094144896 hasConceptScore W2094144896C181199279 @default.
• W2094144896 hasConceptScore W2094144896C185592680 @default.
• W2094144896 hasConceptScore W2094144896C2775970874 @default.
• W2094144896 hasConceptScore W2094144896C2776448209 @default.
• W2094144896 hasConceptScore W2094144896C2776992908 @default.
• W2094144896 hasConceptScore W2094144896C2777164284 @default.
• W2094144896 hasConceptScore W2094144896C2777335581 @default.
• W2094144896 hasConceptScore W2094144896C2777911890 @default.
• W2094144896 hasConceptScore W2094144896C2778163477 @default.
• W2094144896 hasConceptScore W2094144896C2778656385 @default.

• next