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8. 1H and 13C NMR data for 13C-labeled compounds 18–23:
18: 1H NMR (D2O, 500 MHz) 3.95 (1H, dddd, J4,3ax=11.9
H, J4,3eq=5.0 Hz, J4,5=10.4 Hz, J4,C=1.6 Hz, H-4), 3.93
(1H, dd, J6,5=10.4 Hz, J6,7=1.0 Hz, H-6), 3.80 (1H, dd,
H-5), 3.71 (1H, ddd, J9,8=2.8 Hz, J9,9%=11.9 Hz, J9,C
=
144.8 Hz, H-9), 3.62 (1H, dddd, J9%,8=6.4 Hz, H-8), 3.50
(1H, ddd, J9%,C=143.8 Hz, H-9%), 3.43 (1H, dd, J7,8=9.2
Hz, H-7), 2.19 (1H, ddd, J3eq,3ax=12.4 Hz, J3eq,C=132.4
Figure 2. HMQC–HOHAHA spectrum of a 1:1 mixture of
[3-13C]- and [9-13C]-NeuAc.
Hz, H-3eq), 1.92 (3H, s, -NHAc), 1.76 (1H, dddz, J3ax,C
=
130.0 Hz, H-3ax); 13C NMR (D2O, 125 MHz) 64.12 (C-9),
40.20 (C-3); 19: 1H NMR (D2O, 500 MHz) 3.88 (1H,
dddd, J4,3ax=11.6 Hz, J4,3eq=4.9 Hz, J4,5=9.5 Hz, J4,C
2.1 Hz, H-4), 3.84 (1H, dd, J6,5=9.5 Hz, J6,7=1.2 Hz,
H-6), 3.78 (1H, ddd, J9,C=143.1 Hz, J9,8=2.8 Hz, J9,9%
=
=
11.6 Hz, H-9), 3.75 (1H, dd, J7,8=8.9 Hz, H-7), 3.67 (1H,
ddd, J8,9%=6.4 Hz, H-8), 3.57 (1H, ddd, J9%,C=142.8 Hz,
H-9%), 3.49 (1H, dd, H-5), 2.10 (1H, ddd, J3eq,3ax=13.0 Hz,
J
3eq,C=132.4 Hz, H-3eq), 1.66 (1H, ddd, J3ax,C=128.8 Hz,
H-3ax); 13C NMR (D2O, 125 MHz) 63.5 (C-9), 39.25
(C-3); 20: 1H NMR (D2O, 500 MHz) 3.91 (1H, dddd,
J
4,3ax=11.9 Hz, J4,3eq=4.6 Hz, J4,5=10.4 Hz, J4,C=1.6
Hz, H-4), 3.89 (1H, dd, J6,5=10.4 Hz, J6,7=1.0 Hz, H-6),
3.80 (1H, dd, H-5), 3.73 (1H, dd, J9,8=2.4 Hz, J9,9%=11.9
Hz, H-9), 3.65 (1H, ddd, J8,7=9.2 Hz, J8,9%=6.4 Hz, H-8),
3.51 (1H, dd, H-9%), 3.42 (1H, br dd, H-7), 2.12 (1H, ddd,
J
3eq,3ax=12.8 Hz, J3eq,C=132.8 Hz, H-3eq), 1.95 (3H, s,
Figure 3. HMQC–HOHAHA spectrum of a 1:1 mixture of
-NHAc), 1.73 (1H, ddd, J3ax,C=129.4 Hz, H-3ax); 13C
[3-13C]- and [9-13C]-NeuAc (expansion).
1
NMR (D2O, 125 MHz) 39.67 (C-3); 21: H NMR (D2O,
500 MHz) 3.92 (1H, ddd, J4,3ax=10.0 Hz, J4,3eq=4.9 Hz,
Acknowledgements
J4,5=10.1 Hz, H-4), 3.88 (1H, dd, J6,5=10.4 Hz, J6,7=1.0
Hz, H-6), 3.81 (1H, dd, H-5), 3.73 (1H, ddd, J9,8=2.8 Hz,
J9,9%=11.9 Hz, J9,C=144.0 Hz, H-9), 3.66 (1H, ddd, H-8),
3.50 (1H, ddd, J9%,8=6.4 Hz, J9%,C=138.9 Hz, H-9%), 3.41
(1H, br dd, J7,8=9.2 Hz, H-7), 2.11 (1H, dd, J3eq,3ax=13.1
Hz, H-3eq), 1.95 (3H, s, -NHAc), 1.73 (1H, dd, H-3ax);
13C NMR (D2O, 125 MHz) 64.11 (C-9); 22: 1H NMR
This work was partly supported by ‘High-Tech
Research Center Project’ of Ministry of Education,
Science, Sports, and Culture, Japan. The authors thank
Professor Y. Kajihara of Yokohama City University
for NMR measurements.
(D2O, 500 MHz) 3.83 (1H, dddd, J4,3ax=12.0 Hz, J4,3eq
5.2 Hz, J4,5=9.7 Hz, J4,C=2.0 Hz, H-4), 3.79 (1H, dd,
6,5=9.7 Hz, J6,7=1.2 Hz, H-6), 3.68 (1H, dd, J9,8=2.8
=
J
Hz, J9,9%=11.5 Hz, H-9), 3.70 (1H, dd, J7,8=8.9 Hz, H-7),
3.65 (1H, ddd, J8,9%=6.3 Hz, H-8), 3.50 (1H, dd, H-9%),
3.43 (1H, dd, H-5), 2.05 (1H, ddd, J3eq,3ax=13.2 Hz,
References
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