Matches in SemOpenAlex for { <https://semopenalex.org/work/W3215660167> ?p ?o ?g. }
- W3215660167 abstract "Finding convenient ways for the stereoselective α-sialylation is important due to the high practical significance of α-sialic acid-containing glycans and neoglycoconjugates. It was proposed that sialylation stereoselectivity is determined by the structure of the sialyl cation (also known in biochemistry as sialosyl cation), a supposed intermediate in this reaction. Here we design a new approach for studying the conformational space of highly flexible sialyl cation and find 1625 unique conformers including those stabilized by covalent remote participation (also known as long-range participation) of 4-O-acetyl (4-OAc), 5-N-trifluoroacetyl (5-NTFA), as well as 7,8,9-OAc from both α and β sides. The most energetically stable sialyl cation conformers are featured by 4-OAc participation, closely followed by 5-NTFA- and 7-OAc-stabilized conformers; unstabilized sialyl cation conformers are ∼10 kcal mol-1 less stable than the 4-OAc-stabilized ones. Analysis of all the obtained conformers by means of substituents positions, side chain conformations and ring puckering led us to a new eight-conformer hypothesis which describes interconversions among the most important sialyl cation conformers and predicts that stronger remote participation of acyl groups favors β-anomers. Thus, selective synthesis of the desired α-sialosides requires minimization of acyl groups participation." @default.
- W3215660167 created "2021-12-06" @default.
- W3215660167 creator A5006079745 @default.
- W3215660167 creator A5009208122 @default.
- W3215660167 creator A5014408190 @default.
- W3215660167 creator A5033771889 @default.
- W3215660167 date "2021-12-16" @default.
- W3215660167 modified "2023-09-25" @default.
- W3215660167 title "Exhaustive Conformational Search for Sialyl Cation Reveals Possibility of Remote Participation of Acyl Groups" @default.
- W3215660167 cites W1481831422 @default.
- W3215660167 cites W151377110 @default.
- W3215660167 cites W1579160698 @default.
- W3215660167 cites W1938656015 @default.
- W3215660167 cites W1968374685 @default.
- W3215660167 cites W1976292358 @default.
- W3215660167 cites W1980436908 @default.
- W3215660167 cites W1981871976 @default.
- W3215660167 cites W1989731401 @default.
- W3215660167 cites W1991646465 @default.
- W3215660167 cites W1993364167 @default.
- W3215660167 cites W1995510727 @default.
- W3215660167 cites W2008423326 @default.
- W3215660167 cites W2027170262 @default.
- W3215660167 cites W2030072625 @default.
- W3215660167 cites W2034949980 @default.
- W3215660167 cites W2036493629 @default.
- W3215660167 cites W2037112319 @default.
- W3215660167 cites W2037570317 @default.
- W3215660167 cites W2038270516 @default.
- W3215660167 cites W2050102086 @default.
- W3215660167 cites W2052273644 @default.
- W3215660167 cites W2053624404 @default.
- W3215660167 cites W2062415305 @default.
- W3215660167 cites W2063981461 @default.
- W3215660167 cites W2071601554 @default.
- W3215660167 cites W2073889408 @default.
- W3215660167 cites W2078166544 @default.
- W3215660167 cites W2084391380 @default.
- W3215660167 cites W2087062984 @default.
- W3215660167 cites W2092157292 @default.
- W3215660167 cites W2096666086 @default.
- W3215660167 cites W2148481005 @default.
- W3215660167 cites W2153474295 @default.
- W3215660167 cites W2157917527 @default.
- W3215660167 cites W2165974964 @default.
- W3215660167 cites W2166891519 @default.
- W3215660167 cites W2256783395 @default.
- W3215660167 cites W2319279765 @default.
- W3215660167 cites W2519294819 @default.
- W3215660167 cites W2522666470 @default.
- W3215660167 cites W2543022866 @default.
- W3215660167 cites W2557113729 @default.
- W3215660167 cites W2567896191 @default.
- W3215660167 cites W2639728117 @default.
- W3215660167 cites W2753165348 @default.
- W3215660167 cites W2765538933 @default.
- W3215660167 cites W2791394133 @default.
- W3215660167 cites W2797395466 @default.
- W3215660167 cites W2800150946 @default.
- W3215660167 cites W2805738781 @default.
- W3215660167 cites W2888445694 @default.
- W3215660167 cites W2894629617 @default.
- W3215660167 cites W2900350036 @default.
- W3215660167 cites W2901036203 @default.
- W3215660167 cites W2939865878 @default.
- W3215660167 cites W2962784850 @default.
- W3215660167 cites W2982437619 @default.
- W3215660167 cites W3020719222 @default.
- W3215660167 cites W3038902560 @default.
- W3215660167 cites W3092172462 @default.
- W3215660167 cites W3114618044 @default.
- W3215660167 cites W3122865608 @default.
- W3215660167 cites W3127055491 @default.
- W3215660167 cites W3157649705 @default.
- W3215660167 cites W4211178606 @default.
- W3215660167 cites W4245229812 @default.
- W3215660167 cites W52093646 @default.
- W3215660167 doi "https://doi.org/10.1002/cphc.202100788" @default.
- W3215660167 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/34837303" @default.
- W3215660167 hasPublicationYear "2021" @default.
- W3215660167 type Work @default.
- W3215660167 sameAs 3215660167 @default.
- W3215660167 citedByCount "2" @default.
- W3215660167 countsByYear W32156601672022 @default.
- W3215660167 crossrefType "journal-article" @default.
- W3215660167 hasAuthorship W3215660167A5006079745 @default.
- W3215660167 hasAuthorship W3215660167A5009208122 @default.
- W3215660167 hasAuthorship W3215660167A5014408190 @default.
- W3215660167 hasAuthorship W3215660167A5033771889 @default.
- W3215660167 hasConcept C108625454 @default.
- W3215660167 hasConcept C161790260 @default.
- W3215660167 hasConcept C178790620 @default.
- W3215660167 hasConcept C181647583 @default.
- W3215660167 hasConcept C185592680 @default.
- W3215660167 hasConcept C18705241 @default.
- W3215660167 hasConcept C206212055 @default.
- W3215660167 hasConcept C2780115458 @default.
- W3215660167 hasConcept C2780378348 @default.
- W3215660167 hasConcept C32909587 @default.
- W3215660167 hasConcept C55493867 @default.