Matches in SemOpenAlex for { <https://semopenalex.org/work/W2047536144> ?p ?o ?g. }
Showing items 1 to 84 of
84
with 100 items per page.
- W2047536144 endingPage "15751" @default.
- W2047536144 startingPage "15750" @default.
- W2047536144 abstract "The first committed biosynthetic step toward clavulanic acid, the clinically important β-lactamase inhibitor, is catalyzed by the thiamin diphosphate (ThDP)-dependent enzyme N2-(2-carboxyethyl)arginine synthase (CEAS). This protein carries out a unique reaction among ThDP-dependent processes in which a C−N bond is formed, and an electrophilic acryloyl−thiazolium intermediate of ThDP is proposed to be involved, unlike the nucleophilic enamine species typically generated by this class of enzymes. Here we present evidence for the existence of the putative acryloyl adduct and report the unexpected observation of a long-wavelength chromophore (λ = 433 nm), which we attribute to this enzyme-bound species. Chemical models were synthesized that both confirm its expected absorption (λ = 310−320 nm) and exclude self-condensation and intramolecular imine formation with the cofactor as its cause. Circular dichroism experiments and others discount charge transfer as a likely explanation for the ∼120 nm red shift of the chromophore (∼25 kcal). Examples are well-known of charged molecules that exhibit significantly red-shifted UV−visible spectra compared to their neutral forms as, for example, polyene cations and dyes such as indigo and the cyanines. Rhodopsin is the classic biochemical example where the protein (opsin)-bound protonated Schiff base of retinal displays a remarkable range of red-shifted absorptions modulated by the protein environment. Similar tuning of the chromophoric behavior of the enzyme-bound CEAS acryloyl·ThDP species may be occurring." @default.
- W2047536144 created "2016-06-24" @default.
- W2047536144 creator A5054215880 @default.
- W2047536144 creator A5067252545 @default.
- W2047536144 date "2007-12-01" @default.
- W2047536144 modified "2023-10-11" @default.
- W2047536144 title "Observation of an Acryloyl−Thiamin Diphosphate Adduct in the First Step of Clavulanic Acid Biosynthesis" @default.
- W2047536144 cites W1975117802 @default.
- W2047536144 cites W1991700756 @default.
- W2047536144 cites W1997220351 @default.
- W2047536144 cites W2003090573 @default.
- W2047536144 cites W2005090163 @default.
- W2047536144 cites W2008267534 @default.
- W2047536144 cites W2023535483 @default.
- W2047536144 cites W2037789407 @default.
- W2047536144 cites W2058995008 @default.
- W2047536144 cites W2312994653 @default.
- W2047536144 cites W2322422875 @default.
- W2047536144 cites W2323965037 @default.
- W2047536144 cites W2346681245 @default.
- W2047536144 cites W2952723569 @default.
- W2047536144 doi "https://doi.org/10.1021/ja076704r" @default.
- W2047536144 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/3180866" @default.
- W2047536144 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/18052280" @default.
- W2047536144 hasPublicationYear "2007" @default.
- W2047536144 type Work @default.
- W2047536144 sameAs 2047536144 @default.
- W2047536144 citedByCount "37" @default.
- W2047536144 countsByYear W20475361442012 @default.
- W2047536144 countsByYear W20475361442013 @default.
- W2047536144 countsByYear W20475361442014 @default.
- W2047536144 countsByYear W20475361442015 @default.
- W2047536144 countsByYear W20475361442016 @default.
- W2047536144 countsByYear W20475361442017 @default.
- W2047536144 countsByYear W20475361442019 @default.
- W2047536144 countsByYear W20475361442020 @default.
- W2047536144 countsByYear W20475361442021 @default.
- W2047536144 countsByYear W20475361442023 @default.
- W2047536144 crossrefType "journal-article" @default.
- W2047536144 hasAuthorship W2047536144A5054215880 @default.
- W2047536144 hasAuthorship W2047536144A5067252545 @default.
- W2047536144 hasBestOaLocation W20475361442 @default.
- W2047536144 hasConcept C108204754 @default.
- W2047536144 hasConcept C145148216 @default.
- W2047536144 hasConcept C178790620 @default.
- W2047536144 hasConcept C185592680 @default.
- W2047536144 hasConcept C192468462 @default.
- W2047536144 hasConcept C2779594873 @default.
- W2047536144 hasConcept C30095370 @default.
- W2047536144 hasConcept C71240020 @default.
- W2047536144 hasConcept C75473681 @default.
- W2047536144 hasConceptScore W2047536144C108204754 @default.
- W2047536144 hasConceptScore W2047536144C145148216 @default.
- W2047536144 hasConceptScore W2047536144C178790620 @default.
- W2047536144 hasConceptScore W2047536144C185592680 @default.
- W2047536144 hasConceptScore W2047536144C192468462 @default.
- W2047536144 hasConceptScore W2047536144C2779594873 @default.
- W2047536144 hasConceptScore W2047536144C30095370 @default.
- W2047536144 hasConceptScore W2047536144C71240020 @default.
- W2047536144 hasConceptScore W2047536144C75473681 @default.
- W2047536144 hasIssue "51" @default.
- W2047536144 hasLocation W20475361441 @default.
- W2047536144 hasLocation W20475361442 @default.
- W2047536144 hasLocation W20475361443 @default.
- W2047536144 hasLocation W20475361444 @default.
- W2047536144 hasOpenAccess W2047536144 @default.
- W2047536144 hasPrimaryLocation W20475361441 @default.
- W2047536144 hasRelatedWork W1976617235 @default.
- W2047536144 hasRelatedWork W1992746337 @default.
- W2047536144 hasRelatedWork W2038815086 @default.
- W2047536144 hasRelatedWork W2052303811 @default.
- W2047536144 hasRelatedWork W2067743368 @default.
- W2047536144 hasRelatedWork W2091760715 @default.
- W2047536144 hasRelatedWork W2319782831 @default.
- W2047536144 hasRelatedWork W2783558094 @default.
- W2047536144 hasRelatedWork W2807881618 @default.
- W2047536144 hasRelatedWork W2952528272 @default.
- W2047536144 hasVolume "129" @default.
- W2047536144 isParatext "false" @default.
- W2047536144 isRetracted "false" @default.
- W2047536144 magId "2047536144" @default.
- W2047536144 workType "article" @default.