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- W2022019994 abstract "A facile strategy for the stereoselective synthesis of suitably protected O-glycosylated amino acid building blocks, namely, Nα-Fmoc-Ser-[Ac4-β-d-Gal-(1-3)-Ac2α or β-d-GalN3]-OPfp and Nα-Fmoc-Thr-[Ac4-β-d-Gal-(1-3)-Ac2-α or β-d-GalN3]-OPfp is described. What is new and novel in this report is that Koenigs-Knorr type glycosylation of an aglycon serine/threonine derivative (i.e. Nα-Fmoc-Ser-OPfp or Nα-Fmoc-Thr-OPfp) with protected β-d-Gal(1-3)-d-GalN3 synthon mediated by silver salts resulted in only α-and/or β-isomers in excellent yields under two different reaction conditions. The subtle differences in stereoselectivity were demonstrated clearly when glycosylation was carried out using only AgClO4 at -40°C which afforded α-isomer in a quantitative yield (α:β= 5:1). On the other hand, the β-isomer was formed exclusively when the reaction was performed in the presence of Ag2CO3AgClO4 at room temperature. A complete assignment of 1H resonances to individual sugar ring protons and the characteristic anomeric α-1H and β-1H in Ac4Galβ(1-3)Ac2GalN3α and/or β linked to Ser/Thr building blocks was accomplished unequivocally by two-dimensional double-quantum filtered correlated spectroscopy and nuclear Overhauser enhancement and exchange spectroscopy NMR experiments. An unambiguous structural characterization and documentation of chemical shifts, including the coupling constants for all the protons of the aforementioned a- and p-isomers of the O-glycosylated amino acid building blocks carrying protected β-d-Gal(1-3)-d-GalN3, could serve as a template in elucidating the three-dimensional structure of glycoproteins. The synthetic utility of the building blocks and versatility of the strategy was exemplified in the construction of human salivary mucin (MUC7)-derived, O-linked glycopeptides with varied degrees of glycosylation by solid-phase Fmoc chemistry. Fmoc/tert-butyl-based protecting groups were used for the peptidic" @default.
- W2022019994 created "2016-06-24" @default.
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- W2022019994 date "2009-01-12" @default.
- W2022019994 modified "2023-09-27" @default.
- W2022019994 title "A concise methodology for the stereoselective synthesis of O-glycosylated amino acid building blocks: complete 1HNMR assignments and their application in solid-phase glycopeptide synthesis" @default.
- W2022019994 cites W1492833857 @default.
- W2022019994 cites W1494626566 @default.
- W2022019994 cites W1562194553 @default.
- W2022019994 cites W1571862215 @default.
- W2022019994 cites W1578270753 @default.
- W2022019994 cites W1589735909 @default.
- W2022019994 cites W1965055266 @default.
- W2022019994 cites W1966808355 @default.
- W2022019994 cites W1969438932 @default.
- W2022019994 cites W1972936598 @default.
- W2022019994 cites W1974384968 @default.
- W2022019994 cites W1975797997 @default.
- W2022019994 cites W1978121073 @default.
- W2022019994 cites W1978424754 @default.
- W2022019994 cites W1980354916 @default.
- W2022019994 cites W1981683657 @default.
- W2022019994 cites W1983257000 @default.
- W2022019994 cites W1988072233 @default.
- W2022019994 cites W1990332976 @default.
- W2022019994 cites W1993407840 @default.
- W2022019994 cites W1998331383 @default.
- W2022019994 cites W2003802570 @default.
- W2022019994 cites W2006646770 @default.
- W2022019994 cites W2006850107 @default.
- W2022019994 cites W2010768927 @default.
- W2022019994 cites W2011626909 @default.
- W2022019994 cites W2011713122 @default.
- W2022019994 cites W2015064119 @default.
- W2022019994 cites W2016630695 @default.
- W2022019994 cites W2018940756 @default.
- W2022019994 cites W2021760309 @default.
- W2022019994 cites W2024632215 @default.
- W2022019994 cites W2026305391 @default.
- W2022019994 cites W2029756819 @default.
- W2022019994 cites W2031700300 @default.
- W2022019994 cites W2037150011 @default.
- W2022019994 cites W2037455416 @default.
- W2022019994 cites W2038514890 @default.
- W2022019994 cites W2042614740 @default.
- W2022019994 cites W2044429230 @default.
- W2022019994 cites W2045446885 @default.
- W2022019994 cites W2047572594 @default.
- W2022019994 cites W2048780818 @default.
- W2022019994 cites W2055186032 @default.
- W2022019994 cites W2055973748 @default.
- W2022019994 cites W2058061286 @default.
- W2022019994 cites W2058556221 @default.
- W2022019994 cites W2063302960 @default.
- W2022019994 cites W2064761727 @default.
- W2022019994 cites W2066013978 @default.
- W2022019994 cites W2074770586 @default.
- W2022019994 cites W2075028117 @default.
- W2022019994 cites W2078047823 @default.
- W2022019994 cites W2083214508 @default.
- W2022019994 cites W2085384400 @default.
- W2022019994 cites W2087620315 @default.
- W2022019994 cites W2088533705 @default.
- W2022019994 cites W2093702974 @default.
- W2022019994 cites W2107768544 @default.
- W2022019994 cites W2117745698 @default.
- W2022019994 cites W2123072024 @default.
- W2022019994 cites W2123511654 @default.
- W2022019994 cites W2126954508 @default.
- W2022019994 cites W2129232972 @default.
- W2022019994 cites W2150316114 @default.
- W2022019994 cites W2152708819 @default.
- W2022019994 cites W2317905558 @default.
- W2022019994 cites W2338694799 @default.
- W2022019994 cites W2419621050 @default.
- W2022019994 cites W2949250147 @default.
- W2022019994 cites W2949344901 @default.
- W2022019994 cites W2951601453 @default.
- W2022019994 cites W3023239546 @default.
- W2022019994 cites W4206701382 @default.
- W2022019994 cites W4231731508 @default.
- W2022019994 cites W47285420 @default.
- W2022019994 doi "https://doi.org/10.1111/j.1399-3011.1998.tb01473.x" @default.
- W2022019994 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/9774229" @default.
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