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Correction: Synthesis and application of a highly branched, mechanism-based 2-deoxy-2-fluoro-oligosaccharide inhibitor of endo-xyloglucanases

Namrata Jainab, Mohamed A. Attiaab, Wendy A. Offenc, Gideon J. Daviesc 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

Received 28th November 2018 , Accepted 28th November 2018

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.


The authors regret that the 1H and 13C NMR chemical shift values for compounds 2, 4, and 5, as well as the 19F NMR values of compound 5, were incorrectly reported in the main text of the originally published version of the article. The correct data are listed below, including the original 19F NMR assignment for compound 4. The corresponding spectra were correctly displayed in the Electronic Supplementary Information (ESI) and remain unchanged by this correction.

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).

The Royal Society of Chemistry apologises for these errors and any consequent inconvenience to authors and readers.


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