RSC Advances
Paper
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5.42-5.39 (m, 1H, H-10), 4.59 (s, 1H, H-3), 4.14 (s, 1H, H-4),
4.05–3.95 (m, 2H, H-5a,b), 3.71 (d, J ¼ 9.6 Hz, 1H, H-50),
3.66 (d, J ¼ 12.6 Hz, 1H, H-6a0), 3.60 (t, J ¼ 9.6 Hz, 1H, H-
30), 3.56 (dd, J ¼ 12.6, 4.2 Hz, 1H, H-6b0), 3.33 (d, J ¼
9.6 Hz, 1H, H-20), 3.26 (t, J ¼ 9.6 Hz, 1H, H-40), 2.70-2.64
(m, 1H, H-2), 2.47–2.41 (m, 1H, H-2); 13C NMR (150 MHz,
D2O): d 155.11, 152.05, 148.63, 139.97, 118.55, 95.45 (d, J ¼
6.6 Hz, C-10), 85.65 (d, J ¼ 9.0 Hz, C-4), 83.67 (C-1), 72.73
(C-50), 72.67 (C-30), 71.52 (d, J ¼ 8.7 Hz, C-20), 71.14 (C-3),
69.10 (C-40), 65.35 (d, J ¼ 6.0 Hz, C-5), 60.22 (C-60), 38.97
(C-2); 31P NMR (243 MHz, D2O): d ꢀ11.22 (d, J ¼ 20.7 Hz),
ꢀ12.97 (d, J ¼ 20.7 Hz); ESI-TOF HRMS m/z calcd for
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1
28 Spectroscopic data of dCDP-Glc: H NMR (600 MHz, D2O):
d 7.91 (d, J ¼ 7.8 Hz, 1H, –CH]), 6.13 (t, J ¼ 6.6 Hz, 1H,
H-1), 6.03 (d, J ¼ 7.8 Hz, 1H, –CH]), 5.42 (dd, J ¼ 7.2,
3.0 Hz, 1H, H-10), 4.43 (br s, H-3), 4.09–3.97 (m, 3H, H-4,
H-5a,b), 3.72 (br d, J ¼ 9.6 Hz, 1H, H-50), 3.68 (d, J ¼
12.6 Hz, 1H, H-6a0), 3.63-3.56 (m, 2H, H-30, H-6b0), 3.35 (br
d, J ¼ 9.6 Hz, 1H, H-20), 3.29 (t, J ¼ 9.6 Hz, 1H, H-40), 2.32–
2.25 (m, 1H, H-2), 2.20–2.13 (m, 1H, H-2); 13C NMR (150
MHz, D2O): d 162.83, 142.76, 95.77, 95.46 (d, J ¼ 6.6 Hz, C-
10), 86.19 (C-1), 85.64 (d, J ¼ 9.0 Hz, C-4), 72.75 (C-30),
72.68 (C-50), 71.51 (d, J ¼ 8.4 Hz, C-20), 70.59 (C-3), 69.05
(C-40), 65.11 (C-5), 60.18 (C-60), 39.41 (C-2); 31P NMR (243
MHz, D2O): d ꢀ11.34 (d, J ¼ 20.8 Hz), ꢀ12.99 (d, J ¼ 20.8
Hz); ESI-TOF HRMS m/z calcd for C15H24N3O15P2 [M ꢀ
H]ꢀ1 548.0688, found 548.0616. dGDP-Glc: 1H NMR (600
MHz, D2O): d 7.92 (s, 1H, –CH]), 6.15 (t, J ¼ 7.2 Hz, 1H,
H-1), 5.40 (dd, J ¼ 6.6, 3.0 Hz, 1H, H-10), 4.58 (br s, 1H, H-
3), 4.08 (br s, 1H, H-4), 4.01–3.96 (m, 2H, H-5a,b), 3.74–
3.69 (m, 1H, H-50), 3.67 (d, J ¼ 12.6 Hz, 1H, H-6a0), 3.62–
3.54 (m, 2H, H-30, H-6b0), 3.36–3.31 (m, 1H, H-20), 3.27 (t, J
¼ 9.6 Hz, 1H, H-40), 2.68–2.60 (m, 1H, H-2a), 2.38–2.30 (m,
1H, H-2b); 13C NMR (150 MHz, D2O): d 158.89, 153.75,
151.34, 137.52, 116.11, 95.45 (d, J ¼ 7.5 Hz, C-10), 85.46 (d,
J ¼ 9.0 Hz, C-4), 83.49 (C-1), 72.70 (C-30), 72.66 (C-50), 71.49
(d, J ¼ 9.0 Hz, C-20), 71.22 (C-3), 69.07 (C-40), 65.37 (C-5),
60.19 (C-60), 38.37 (C-2); 31P NMR (243 MHz, D2O):
d ꢀ11.22 (d, J ¼ 20.6 Hz), ꢀ12.99 (d, J ¼ 20.6 Hz); ESI-TOF
HRMS m/z calcd for C16H24N5O15P2 [M ꢀ H]ꢀ1 588.0750,
found 588.0680. dADP-Glc: 1H NMR (600 MHz, D2O):
d 8.32 (s, 1H), 8.09 (s, 1H), 6.36 (t, J ¼ 6.6 Hz, 1H, H-1),
C
16H24N5O14P2 [M
ꢀ
H]ꢀ1 572.0800, found 572.0728.
dTDP-GlcNH2: 1H NMR (600 MHz, D2O): d 7.55 (s, 1H,
–CH]), 6.17 (t, J ¼ 7.2 Hz, 1H, H-1), 5.66 (dd, J ¼ 6.6,
3.0 Hz, 1H, H-10), 4.44 (br s, 1H, H-3), 4.05–3.98 (m, 3H, H-
4, H-5a,b), 3.78–3.72 (m, 2H, H-30, H-50), 3.70 (d, J ¼
12.6 Hz, 1H, H-6a0), 3.64 (dd, J ¼ 12.6, 3.6 Hz, 1H, H-6b0),
3.38 (t, J ¼ 9.6 Hz, 1H, H-40), 3.18 (br d, J ¼ 10.2 Hz, 1H,
H-20), 2.25–2.16 (m, 2H, H-2a,b), 1.75 (s, 3H, –CH3); 13C
NMR (150 MHz, D2O): d 166.49, 151.64, 137.21, 111.62,
92.72 (d, J ¼ 4.5 Hz, C-10), 85.13 (d, J ¼ 9.0 Hz, C-4), 84.94
(C-1), 73.11 (C-50), 70.82 (C-3), 69.74 (C-30), 68.94 (C-40),
65.51 (d, J ¼ 4.5 Hz, C-5), 59.86 (C-6), 54.04 (d, J ¼ 9.0 Hz,
C-20), 38.49 (C-2), 11.54 (–CH3); 31P NMR (243 MHz, D2O):
d ꢀ11.34 (d, J ¼ 21.0 Hz), ꢀ13.75 (d, J ¼ 21.0 Hz); ESI-TOF
HRMS m/z calcd for C16H26N3O15P2 [M ꢀ H]ꢀ1 562.0850,
found 562.0776. dUDP-Gal: d 7.80 (d, J ¼ 7.8 Hz, 1H,
–CH]), 6.18 (t, J ¼ 6.6 Hz, 1H, H-1), 5.81 (d, J ¼ 7.8 Hz,
1H, –CH]), 5.45 (dd, J ¼ 7.2, 3.6 Hz, 1H, H-10), 4.50–4.44
(m, 1H, H-3), 4.08–3.98 (m, 4H, H-4, H-5a,b, H-50), 3.88 (d,
J ¼ 3.0 Hz, 1H, H-40), 3.76 (dd, J ¼ 10.2, 3.0 Hz, 1H, H-30),
3.67–3.63 (m, 1H, H-20), 3.63–3.55 (m, 2H, H-6a,b0), 2.28–
2.19 (m, 2H, H-2a,b); 13C NMR (150 MHz, D2O): d 166.23,
151.55, 141.81, 102.40, 95.74 (d, J ¼ 7.5 Hz, C-10), 85.42 (d,
J ¼ 9.0 Hz, H-4), 85.32 (C-1), 71.81 (C-50), 70.79 (C-3), 69.23
(C-30), 69.01 (C-40), 68.33 (d, J ¼ 9.0 Hz, C-20), 65.29 (d, J ¼
6.0 Hz, C-5), 60.91 (C-60), 38.76 (C-2); 31P NMR (243 MHz,
D2O): d ꢀ11.20 (d, J ¼ 19.4 Hz), ꢀ12.77 (d, J ¼ 19.4 Hz);
ESI-TOF HRMS m/z calcd for C15H24N2O16P2 [M ꢀ H]ꢀ1
549.0528, found 565.0449.
30114 | RSC Adv., 2020, 10, 30110–30114
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