Matches in SemOpenAlex for { <https://semopenalex.org/work/W2073131778> ?p ?o ?g. }
Showing items 1 to 86 of
86
with 100 items per page.
- W2073131778 endingPage "5066" @default.
- W2073131778 startingPage "5056" @default.
- W2073131778 abstract "The mechanism of hydrolysis of the model N-formyltryptophanamide (FmTrp-NH2) with the [Pd(en)]2+ (en = H2NC2H4NH2) complex has been theoretically examined by means of the density functional method (B3LYP). The calculations showed that the N-formyltryptophanamide easily binds to the [Pd(en)]2+ complex to form the stereochemically stable six-membered ring in 2c, where not only the carbonyl oxygen but also the indole carbon interact with the Pd atom. This interaction between the [Pd(en)]2+ and the N-formyltryptophanamide is kept during the hydrolysis reaction to stabilize the energy surface and to reduce the energy barrier. On the other hand, the seven-membered ring formed by the coordination of the C-terminal amide oxygen to the Pd atom instead of the N-terminal amide oxygen was unfavorable in energy. The positive charge of the N-terminal amide carbon is remarkably enhanced by the formation of the Pd-binding cis-[Pd(en)C,O-FmTrp-NH2)]2+ 2c and is selectively attacked by the negatively charged water oxygen, the electron being transferred from the water to the [Pd(en)]2+ complex through the amide CO to promote the hydrolysis reaction. The positive charge of the water hydrogen remarkably increases in the transition state, so that the O−H bond is heterolytically broken and the H+ migrates to the amide nitrogen. When the water attacks the C-terminal amide carbon in 2c, such electron transfer is largely reduced and then the energy barrier increases. Thus, the regioselectivity experimentally observed was reasonably understood by the selective attack of water to the N-terminal amide carbon. It was also found that the stability of the potential energy surface and the energy barrier of the hydrolysis reaction can be controlled by the strength of the electron donation of the ligand of the Pd complex." @default.
- W2073131778 created "2016-06-24" @default.
- W2073131778 creator A5077337547 @default.
- W2073131778 creator A5090818288 @default.
- W2073131778 date "2001-10-02" @default.
- W2073131778 modified "2023-09-24" @default.
- W2073131778 title "Density Functional Study on Regioselective Hydrolysis of a Tryptophan-Containing Peptide Promoted by Palladium(II) Complexes" @default.
- W2073131778 cites W1963737263 @default.
- W2073131778 cites W1964837435 @default.
- W2073131778 cites W1966182479 @default.
- W2073131778 cites W1968381941 @default.
- W2073131778 cites W2002203770 @default.
- W2073131778 cites W2008893554 @default.
- W2073131778 cites W2011475011 @default.
- W2073131778 cites W2018842324 @default.
- W2073131778 cites W2023271753 @default.
- W2073131778 cites W2025830147 @default.
- W2073131778 cites W2029867653 @default.
- W2073131778 cites W2033990154 @default.
- W2073131778 cites W2044490585 @default.
- W2073131778 cites W2058504095 @default.
- W2073131778 cites W2086502645 @default.
- W2073131778 cites W2143981217 @default.
- W2073131778 cites W2149469850 @default.
- W2073131778 cites W2164168511 @default.
- W2073131778 cites W4237427979 @default.
- W2073131778 cites W4241965067 @default.
- W2073131778 cites W4244238393 @default.
- W2073131778 cites W4253803510 @default.
- W2073131778 doi "https://doi.org/10.1021/om0105021" @default.
- W2073131778 hasPublicationYear "2001" @default.
- W2073131778 type Work @default.
- W2073131778 sameAs 2073131778 @default.
- W2073131778 citedByCount "9" @default.
- W2073131778 countsByYear W20731317782015 @default.
- W2073131778 countsByYear W20731317782020 @default.
- W2073131778 crossrefType "journal-article" @default.
- W2073131778 hasAuthorship W2073131778A5077337547 @default.
- W2073131778 hasAuthorship W2073131778A5090818288 @default.
- W2073131778 hasConcept C147597530 @default.
- W2073131778 hasConcept C152365726 @default.
- W2073131778 hasConcept C155647269 @default.
- W2073131778 hasConcept C161790260 @default.
- W2073131778 hasConcept C178790620 @default.
- W2073131778 hasConcept C185592680 @default.
- W2073131778 hasConcept C2778439535 @default.
- W2073131778 hasConcept C502130503 @default.
- W2073131778 hasConcept C540031477 @default.
- W2073131778 hasConcept C59759590 @default.
- W2073131778 hasConcept C71240020 @default.
- W2073131778 hasConcept C75473681 @default.
- W2073131778 hasConcept C94412978 @default.
- W2073131778 hasConceptScore W2073131778C147597530 @default.
- W2073131778 hasConceptScore W2073131778C152365726 @default.
- W2073131778 hasConceptScore W2073131778C155647269 @default.
- W2073131778 hasConceptScore W2073131778C161790260 @default.
- W2073131778 hasConceptScore W2073131778C178790620 @default.
- W2073131778 hasConceptScore W2073131778C185592680 @default.
- W2073131778 hasConceptScore W2073131778C2778439535 @default.
- W2073131778 hasConceptScore W2073131778C502130503 @default.
- W2073131778 hasConceptScore W2073131778C540031477 @default.
- W2073131778 hasConceptScore W2073131778C59759590 @default.
- W2073131778 hasConceptScore W2073131778C71240020 @default.
- W2073131778 hasConceptScore W2073131778C75473681 @default.
- W2073131778 hasConceptScore W2073131778C94412978 @default.
- W2073131778 hasIssue "24" @default.
- W2073131778 hasLocation W20731317781 @default.
- W2073131778 hasOpenAccess W2073131778 @default.
- W2073131778 hasPrimaryLocation W20731317781 @default.
- W2073131778 hasRelatedWork W1979023840 @default.
- W2073131778 hasRelatedWork W1989504973 @default.
- W2073131778 hasRelatedWork W2097014657 @default.
- W2073131778 hasRelatedWork W2188446125 @default.
- W2073131778 hasRelatedWork W2329867129 @default.
- W2073131778 hasRelatedWork W2332347605 @default.
- W2073131778 hasRelatedWork W2890185961 @default.
- W2073131778 hasRelatedWork W2949789655 @default.
- W2073131778 hasRelatedWork W2950458493 @default.
- W2073131778 hasRelatedWork W2972302527 @default.
- W2073131778 hasVolume "20" @default.
- W2073131778 isParatext "false" @default.
- W2073131778 isRetracted "false" @default.
- W2073131778 magId "2073131778" @default.
- W2073131778 workType "article" @default.