2001
DOI: 10.1002/1521-3773(20010917)40:18<3447::aid-anie3447>3.0.co;2-8
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A Free-Energy Relationship between the Rate of Acidic Hydrolysis of Glycosides and the pKa of Isofagomines

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Cited by 75 publications
(47 citation statements)
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References 23 publications
(10 reference statements)
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“…By comparing the p K a values for the conjugate acid it was found that equatorial substituents are significantly more deactivating (EWD) than their axial counterparts. 25,26,27,28 The same effects were found for glycosyl donors and used by Bols and co-workers to conformationally arm glycosyl donors by changing the equatorial rich 4 C 1 conformation to an axial rich conformation. 29,30,31,32,33 The conformational changes were induced by creating steric congestion at the equatorial C-2, C-3 and C-4 positions of D-glucosides, 34 resulting in a skew-boat conformation (donor B1 , Scheme 1B).…”
supporting
confidence: 60%
“…By comparing the p K a values for the conjugate acid it was found that equatorial substituents are significantly more deactivating (EWD) than their axial counterparts. 25,26,27,28 The same effects were found for glycosyl donors and used by Bols and co-workers to conformationally arm glycosyl donors by changing the equatorial rich 4 C 1 conformation to an axial rich conformation. 29,30,31,32,33 The conformational changes were induced by creating steric congestion at the equatorial C-2, C-3 and C-4 positions of D-glucosides, 34 resulting in a skew-boat conformation (donor B1 , Scheme 1B).…”
supporting
confidence: 60%
“…Judging from the K d value of 3 (0.76 M), the compound appears to have the highest affinity among the lysozyme inhibitors identified to date. The pH dependence of ⌬G r°f or 3 (Table 4) might be derived from the change in the protonation state of the moranoline moiety, of which the pK a value was reported to be 6.3-6.7 (13,31). The protonation state of Glu-35 (pK a ϭ 6.7, Ref.…”
Section: Discussionmentioning
confidence: 99%
“…33 In contrast, a correlation has been observed between the reactivity and electronegativity of ring substituents. 24 In the case of furanosides the sugar ring configuration correlates more clearly with the reactivity. The substituents of adjacent carbon atoms in cis orientation can be expected to repel each other, and this repulsion is relieved as the sugar ring is opened and an acyclic oxocarbenium ion is formed.…”
Section: Discussionmentioning
confidence: 99%