Namrata
Jain
ab,
Mohamed A.
Attia
ab,
Wendy A.
Offen
c,
Gideon J.
Davies
c and
Harry
Brumer
*abd
aMichael Smith Laboratories, University of British Columbia, 2185 East Mall, Vancouver, British Columbia V6T 1Z4, Canada. E-mail: brumer@msl.ubc.ca; Fax: (+1) 6048222114; Tel: (+1) 6048273738
bDepartment of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia V6T 1Z1, Canada
cDepartment of Chemistry, University of York, Heslington, York YO10 5DD, UK
dDepartment of Biochemistry and Molecular Biology, University of British Columbia, 2350 Health Sciences Mall, Vancouver, British Columbia V6T 1Z3, Canada
First published on 6th December 2018
Correction for ‘Synthesis and application of a highly branched, mechanism-based 2-deoxy-2-fluoro-oligosaccharide inhibitor of endo-xyloglucanases’ by Namrata Jain et al., Org. Biomol. Chem., 2018, 16, 8732–8741.
Per-O-acetylated XXXG glycal (2):
1H-NMR (Fig. S1,† 400 MHz, CDCl3): δ 6.41 (d, J = 6.14 Hz, 1H, H1), 5.40–5.36 (m), 5.19–4.60 (m), 4.29–3.65 (m), 3.35 (d), 2.13–1.93 (54H, COCH3). 13C-NMR (Fig. S2,† 100.6 MHz, CDCl3): δ 170.34–168.64 (18 × CO), 145.58 (C1), 101.07–95.94 (C2, 6 × C1), 75.66–67.17 (6 × C2, 7 × C3, 7 × C4, 7 × C5), 61.77, 59.22, 59.06, 58.85 (4 × C6), 20.80–20.65 (18 × CH3).
Per-O-acetylated 2′4′-dinitrophenyl β-glycoside of 2-deoxy-2-fluoro-XXXG (4):
1H-NMR (Fig. S4,† 400 MHz, CDCl3): δ 8.75 (d, 1H, H′3), 8.45 (dd, 1H, H′5), 7.42 (d, 1H, H′6), 5.56 (d, 1H, H1), 5.43–5.32 (m), 5.17–4.60 (m), 4.15–3.68 (m), 3.43 (d), 2.16–1.97 (54H, COCH3). 13C-NMR (Fig. S5,† 100.6 MHz, CDCl3): δ 170.23–168.56 (18 × CO), 153.22 (C′3), 142.00 (C′4), 140.01 (C′5), 128.65 (C′1), 121.54 (C′2), 117.49 (C′6), 100.38–95.91 (7 × C1), 88.09 (JC2–F2 = 189.0 Hz, C2), 75.22–67.32 (6 × C2, 7 × C3, 7 × C4, 7 × C5), 60.40, 59.09, 58.94, 58.74 (4 × C6), 21.05–20.58 (18 × CH3). 19F-NMR (Fig. S6,† 376.5 MHz, CDCl3): δ −194.75 (ddd, JH2–F2 = 47.7 Hz, JH3–F2 = 15.7 Hz, JH1–F2 = 2.5 Hz, F2).
2′4′-Dinitrophenyl β-glycoside of 2-deoxy-2-fluoro-XXXG (XXXG(2F)-β-DNP) (5):
1H-NMR (Fig. S7,† 400 MHz, D2O): δ 8.75 (d, 1H, H′3), 8.51 (dd, 1H, H′5), 7.67 (d, 1H, H′6), 5.66 (d, 1H, H1), 4.84–4.80 (m), 4.61–4.39 (m), 3.98–3.31 (m). 13C-NMR (Fig. S8,† 100.6 MHz, D2O): δ 153.37 (C′3), 141.19 (C′4), 138.42 (C′5), 129.35 (C′1), 121.72 (C′2), 117.32 (C′6), 102.35–96.97 (7 × C1), 90.43 (JC2–F2 = 186.8 Hz, C2), 78.81–65.33 (6 × C2, 7 × C3, 7 × C4, 7 × C5), 61.93, 61.05, 61.00, 60.68 (4 × C6). Small amounts of CD3OD (sep, 47.52) and CH3COONa (181.02, 22.74) were also detected. 19F-NMR (Fig. S9,† 376.5 MHz, D2O): δ −199.69 (ddd, JH2–F2 = 51.4 Hz, JH3–F2 = 15.2 Hz, JH1–F2 = 2.5 Hz, F2).
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