Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007
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1 Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007
2 Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006 Supporting Information for High-Throughput Substrate Specificity Studies of Sialidases by Using Chemoenzymatically Synthesized Sialoside Libraries Harshal Chokhawala, Hai Yu, and Xi Chen* General Methods 1 H NMR (300, 400 or 600 MHz) and 13 C NMR (75 or 100 MHz) spectra were recorded on a Varian Mercury-300, a Varian Inova-400, or a Varian Inova-600 spectrometer. Low and high resolution electrospray ionization (ESI) mass spectra were obtained at the Mass Spectrometry and Proteomics Facility in the Ohio State University. NMR and HRMS Data of Sialosides 4-Nitrophenyl O-(5-acetamido-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonic acid)-(2? 3)-O-b-D-galactopyranoside (Neu5Aca2,3GalbpNP, 8) Yield, 91%; light yellow foam. 1 H NMR (400 MHz, D2O) δ 8.25 (d, 2H, J = 9.2 Hz), 7.23 (d, 2H, J = 9.2 Hz), 5.29 (d, 1H, J = 7.6 Hz), 4.22 (dd, 1H, J = 9.6 and 3.2 Hz), 4.02 (d, 1H, J = 3.2 Hz), (m, 11H), 2.76 (dd, 1H, J = 12.4 and 4.4 Hz, H-3 eq ), 2.00 (s, 3H), 1.80 (t, 1H, J = 12.4 Hz, H-3 ax ); 13 C NMR (100 MHz, D 2 O) δ , , , , (2C), (2C), , , 75.74, 73.16, 72.32, 72.05, 69.07, 68.56, - 1 -
3 68.34, 67.60, 62.78, 60.95, 52.00, 39.94, HRMS (ESI) m/z calcd for C 23 H 31 N 2 O 16 (M-Na) , found Nitrophenyl O-(5-acetamido-9-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonic acid)-(2? 3)-O-b-D-galactopyranoside (Neu5,9Ac2a2,3GalbpNP, 9) Yield, 87%; light yellow foam. 1 H NMR (400 MHz, D 2 O) δ 8.25 (d, 2H, J = 9.2 Hz), 7.24 (d, 2H, J = 9.2 Hz), 5.29 (d, 1H, J = 7.6 Hz), 4.37 (d, 1H, J = 11.6 Hz), 4.23 (d, 1H, J = 9.6 Hz), 4.15 (dd, 1H, J = 12.0 and 5.6 Hz), (m,10h), 2.77 (dd, 1H, J = 12.4 and 4.4 Hz, H-3 eq ), 2.06 (s, 3H), 2.02 (s, 3H), 1.81 (t, 1H, J = 12.4 Hz, H-3 ax ); 13 C NMR (100 MHz, D 2 O) δ , , , , , (2C), (2C), 99.96, 99.81, 75.60, 72.83, 72.18, 69.54, 68.93, 68.51, 67.34, 65.80, 62.59, 60.80, 51.80, 39.85, 22.18, HRMS (ESI) m/z calcd for C 25 H 33 N 2 O 17 (M-Na) , found Nitrophenyl O-(5-acetamido-3,5-dideoxy-9-O-lactyl-D-glycero-a-D-galacto-2-nonulopyranosylonic acid)-(2? 3)-O-b-D-galactopyranoside (Neu5Ac9Lta2,3GalbpNP, 10) Yield, 75%; light yellow foam. 1 H NMR (600 MHz, D 2 O) δ 8.25 (d, 2H, J = 9.0 Hz), 7.24 (d, 2H, J = 9.0 Hz), 5.28 (d, 1H, J = 7.8 Hz), (m, 2H), 4.31 (dd, 1H, J = 12.0 and 5.4 Hz), 4.23 (dd, 1H, J = 9.6 and 3.0 Hz), (m, 1H), 4.03 (d, 1H, J = 3.0 Hz), (m, 8H), 2.77 (dd, 1H, J = 12.6 and 4.8 Hz, H-3 eq ), 2.01 (s, 3H), 1.81 (t, 1H, J = 12.6 Hz, H-3 ax ), 1.35 (d, 3H, J = 7.2 Hz); 13 C NMR (150 MHz, D 2 O) δ , , , , , (2C), (2C), , , 75.66, 72.80, 69.55, 68.41, 68.07, 67.37, 66.74, 66.09, 62.61, 60.82, 59.45, 51.83, 39.88, 22.18, HRMS (ESI) m/z calcd for C 26 H 35 N 2 O 18 (M-Na) , found Nitrophenyl O-(3,5-dideoxy-5-glycolylamido-D-glycero-a-D-galacto-2-nonulopyranosylonic acid)-(2? 3)-O-b-D-galactopyranoside (Neu5Gca2,3GalbpNP, 11) Yield, 76%; light yellow foam. 1 H NMR (400 MHz, D 2 O) δ 8.24 (d, 2H, J = 9.2 Hz), 7.23 (d, 2H, J = 9.2 Hz), 5.28 (d, 1H, J = 7.6 Hz), 4.23 (dd, 1H, J = 9.6 and 2.4 Hz), 4.09 (s, 2H), 4.03 (d, 1H, J = 3.2 Hz), (m, 11H), 2.78 (dd, 1H, J = 12.4 and 4.4 Hz, H-3 eq ), 1.82 (t, 1H, J = 12.4 Hz, H-3ax ); 13 C NMR (100 MHz, D2O) δ , , , , (2C), (2C), , 99.78, (2C), 72.75, 72.00, 68.94, (2C), - 2 -
4 67.39, 62.67, 61.11, 60.80, 51.50, HRMS (ESI) m/z calcd for C 23 H 31 N 2 O 17 (M-Na) , found Nitrophenyl O-(3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosylonic acid)- (2? 3)-O-b-D-galactopyranose (KDNa2,3GalbpNP, 12). Yield, 75%; white foam. 1 H NMR (400 MHz, D2O) δ 8.25 (d, 2H, J = 9.6 Hz), 7.23 (d, 2H, J = 9.6 Hz), 5.28 (d, 1H, J = 8.0 Hz), 4.20 (dd, 1H, J = 9.6 and 2.4 Hz), 4.02 (d, 1H, J = 2.8 Hz), (m, 5H), 3.74 (d, 2H, J = 6.0 Hz), (m, 4H), 2.72 (dd, 1H, J = 12.0 and 4.8 Hz, H-3 ax ), 1.76 (t, 1H, J = 12.0 Hz, H-3 eq ); 13 C NMR (100 MHz, D 2 O) δ 174.1, 161.8, 142.7, (2C), (2C), 100.0, 99.8, 75.6, 75.6, 74.0, 72.3, 70.4, 69.9, 68.9, 67.9, 67.3, 62.8, 60.8, 39.5; HRMS (ESI) m/z calcd for C 21 H 29 NO 16 Na (M+H) , found Nitrophenyl O-(5-acetamido-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonic acid)-(2? 6)-O-b-D-galactopyranoside (Neu5Aca2,6GalbpNP, 13) Yield, 88%; light yellow foam. 1 H NMR (300 MHz, D 2 O) δ 8.27 (d, 2H, J = 7.5 Hz), 7.24 (d, 2H, J = 7.5 Hz), 5.17 (d, 1H, J = 7.8 Hz), (m, 13H), 2.74 (dd, 1H, J = 12.0 and 3.9 Hz, H-3 eq ), 1.99 (s, 3H), 1.80 (t, 1H, J = 12.0 Hz, H-3 ax ); 13 C NMR (75 MHz, D 2 O) δ , , , , (2C), (2C), , 99.99, 74.15, 72.72, 72.48, 71.90, 70.41, 68.55, (2C), 63.16, 62.75, 51.98, 40.40, HRMS (ESI) m/z calcd for C 23 H 31 N 2 O 16 (M-Na) , found Nitrophenyl O-(5-acetamido-9-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonic acid)-(2? 6)-O-b-D-galactopyranoside (Neu5,9Ac 2 a2,6galbpnp, 14) Yield, 78%; light yellow foam. 1 H NMR (300 MHz, D 2 O) δ 8.26 (d, 2H, J = 9.3 Hz), 7.24 (d, 2H, J = 9.3 Hz), 5.16 (d, 1H, J = 7.2 Hz), 4.34 (dd, 1H, J = 11.7 and 2.4 Hz), (m, 12H), 2.73 (dd, 1H, J = 12.0 and 4.8 Hz, H-3 eq ), 2.04 (s, 3H), 1.99 (s, 3H), 1.64 (t, 1H, J = 12.0 Hz, H-3 ax ); 13 C NMR (75 MHz, D 2 O) δ , , , , , (2C), (2C), , , 74.19, 72.47, 72.18, 70.39, 69.36, 68.53, 68.34, 65.83, 63.23, 62.58, 51.93, 40.37, 22.13, HRMS (ESI) m/z calcd for C 25 H 33 N 2 O 17 (M-Na) , found Nitrophenyl O-(5-acetamido-3,5-dideoxy-9-O-lactyl-D-glycero-a-D-galacto-2-nonulopyranosylonic acid)-(2? 6)-O-b-D-galactopyranoside (Neu5Ac9Lta2,6GalbpNP, 15) Yield, 92%; light yellow foam. 1 H NMR (300 MHz, D2O) δ 8.26 (d, 2H, J = 9.3 Hz), - 3 -
5 7.24 (d, 2H, J = 9.3 Hz), 5.16 (d, 1H, J = 8.7 Hz), (m, 2H), (m, 12H), 2.74 (dd, 1H, J = 12.0 and 4.2 Hz, H-3eq ), 1.99 (s,3h), 1.65 (t, 1H, J = 12.0 Hz, H-3ax ), 1.36 (d, 3H, J = 7.2 Hz); 13 C NMR (75 MHz, D 2 O) δ , , , , , (2C), (2C), , , 74.17, 72.48, 72.18, 70.46, 69.32, 68.56, 68.26, 68.09, 66.70, 66.11, 63.21, 51.97, 40.39, 22.16, HRMS (ESI) m/z calcd for C 26 H 35 N 2 O 18 (M-Na) , found Nitrophenyl O-(3,5-dideoxy-5-glycolylamido-D-glycero-a-D-galacto-2-nonulopyranosylonic acid)-(2? 6)-O-b-D-galactopyranoside (Neu5Gca2,6GalbpNP, 16) Yield, 85%; light yellow foam. 1 H NMR (400 MHz, D 2 O) δ 8.27 (d, 2H, J = 9.2 Hz), 7.25 (d, 2H, J = 9.2 Hz), 5.18 (d, 1H, J = 7.6 Hz), 4.08 (s, 2H), (m, 13H), 2.76 (dd, 1H, J = 12.4 and 4.0 Hz, H-3 eq ), 1.65 (t, 1H, J = 12.4 Hz, H-3 ax ); 13 C NMR (75 MHz, D 2 O) δ , , , , (2C), (2C), , 99.98, 74.14, 72.46, 72.18, 71.95, 70.42, 68.54, 68.23, 68.05, 63.15, 62.60, 61.07, 51.67, HRMS (ESI) m/z calcd for C 23 H 31 N 2 O 17 (M-Na) , found Nitrophenyl O-(3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosylonic acid)- (2? 6)-O-b-D-galactopyranose (KDNa2,6GalbpNP, 17). Yield, 79%; white foam. 1 H NMR (300 MHz, D 2 O) δ 8.27 (d, 2H, J = 9.3 Hz), 7.24 (d, 2H, J = 9.3 Hz), 5.16 (d, 1H, J = 7.2 Hz), (m, 13H), 2.68 (dd, 1H, J = 12.0 and 4.8 Hz, H-3 ax ), 1.57 (t, 1H, J = 12.0 Hz, H-3 eq ); 13 C NMR (75 MHz, D 2 O) δ , , , (2C), (2C), , , 74.13, 73.67, 72.44, 72.21, 70.38, 70.23, 69.75, 68.53, 67.91, 62.58, 59.97, 40.00; HRMS (ESI) m/z calcd for C 21 H 29 NO 16 (M-Na) , found Nitrophenyl O-(5-acetamido-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonic acid)-(2? 6)-O-2-acetamido-2-deoxy-b-D-galactopyranoside (Neu5Aca2,6- GalNAcbpNP, 18) Yield, 92%; light yellow foam. 1 H NMR (300 MHz, D 2 O) δ 8.20 (d, 2H, J = 9.0 Hz), 7.15 (d, 2H, J = 9.0 Hz), 5.19 (d, 1H, J = 8.4 Hz), 4.19 (dd, 1H, J = 10.8 and 8.4 Hz), (m, 12H), 2.73 (dd, 1H, J = 12.4 and 4.2 Hz, H-3 eq ), 2.00 (s, 3H), 1.98 (s, 3H), 1.63 (t, 1H, J = 12.4 Hz, H-3ax ); 13 C NMR (75 MHz, D 2O) δ , , , , , (2C), (2C), , 99.09, 74.15, 72.71, 71.88, - 4 -
6 70.59, 69.69, 68.29, 67.68, 63.21, 62.72, 52.18, 51.95, 40.36, 22.27, HRMS (ESI) m/z calcd for C25H34N3O16 (M-Na) , found Nitrophenyl O-(5-acetamido-9-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2- nonulopyranosylonic acid)-(2? 6)-O-2-acetamido-2-deoxy-b-D-galactopyranoside (Neu5,9Ac 2 a2,6galnacbpnp, 19) Yield, 33%; light yellow foam. 1 H NMR (300 MHz, D 2 O) δ 8.26 (d, 2H, J = 9.3 Hz), 7.21 (d, 2H, J = 9.3 Hz), 5.21 (d, 1H, J = 8.4 Hz), 4.37 (d, 1H, J = 12.0 Hz), (m, 12H), 2.75 (dd, 1H, J = 12.0 and 4.2 Hz, H-3 eq ), 2.06 (s, 3H), 2.00 (s, 3H), 1.99 (s, 3H), 1.66 (t, 1H, J = 12.0 Hz, H-3 ax ); 13 C NMR (75 MHz, D 2 O) δ , , , , , , (2C), (2C), , 99.17, 74.28, 72.57, 70.63, 69.85, 69.36, 68.35, 67.74, 65.88, 63.35, 52.21, 51.96, 40.36, 22.27, 22.16, HRMS (ESI) m/z calcd for C 27 H 36 N 3 O 17 (M-Na) , found Nitrophenyl O-(5-acetamido-3,5-dideoxy-9-O-lactyl-D-glycero-a-D-galacto-2- nonulopyranosylonic acid)-(2? 6)-O-2-acetamido-2-deoxy-b-D-galactopyranoside (Neu5Ac9Lta2,6GalNAcbpNP, 20) Yield, 42%; light yellow foam. 1 H NMR (300 MHz, D 2 O) δ 8.25 (d, 2H, J = 9.3 Hz), 7.20 (d, 2H, J = 9.3 Hz), 5.21 (d, 1H, J = 8.7 Hz), (m, 14H), 2.75 (dd, 1H, J = 12.0 and 4.2 Hz, H-3eq ), 2.00 (s, 3H), 1.99 (s, 3H), 1.66 (t, 1H, J = 12.0 Hz, H-3 ax ), 1.37 (d, 3H, J = 6.6 Hz); 13 C NMR (75 MHz, D 2 O) δ , , , , , , (2C), (2C), , 99.19, 74.27, 72.53, 70.64, 69.32, 68.30, 68.17, 67.76, 66.77, 66.13, 63.34, 52.24, 52.00, 40.36, 22.30, 22.15, HRMS (ESI) m/z calcd for C 28 H 38 N 3 O 18 (M-Na) , found Nitrophenyl O-(3,5-dideoxy-5-glycolylamido-D-glycero-a-D-galacto-2-nonulopyranosylonic acid)-(2? 6)-O-2-acetamido-2-deoxy-b-D-galactopyranoside (Neu- 5Gca2,6GalNAcbpNP, 21) Yield, 85%; light yellow foam. 1 H NMR (300 MHz, D 2 O) δ 8.23 (d, 2H, J = 9.6 Hz), 7.17 (d, 2H, J = 9.6 Hz), 5.21 (d, 1H, J = 8.4 Hz), 4.19 (dd, 1H, J = 10.8 and 8.4 Hz), 4.07 (s, 2H), (m, 12H), 2.75 (dd, 1H, J = 12.0, 3.9 Hz, H- 3 eq ), 1.98 (s, 3H), 1.65 (t, 1H, J = 12.0 Hz, H-3 ax ); 13 C NMR (75 MHz, D 2 O) δ , , , , , (2C), (2C), , 99.15, 74.22, 72.48, - 5 -
7 71.97, 70.65, 68.28, 68.08, 67.74, 63.28, 62.74, 61.10, 52.24, 51.70, 40.43, HRMS (ESI) m/z calcd for C25H34N3O17 (M-Na) , found Nitrophenyl O-(3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosylonic acid)- (2? 6)-O-2-acetamido-2-deoxy-b-D-galactopyranoside (KDNa2,6GalNAcbpNP, 22). Yield, 80%; white foam. 1 H NMR (300 MHz, D2O) δ 8.28 (d, 2H, J = 9.3 Hz), 7.22 (d, 2H, J = 9.3 Hz), 5.24 (d, 1H, J = 8.4 Hz), 4.22 (dd, 1H, J = 10.8 and 8.4 Hz), 4.05 (d, 1H, J = 3.6 Hz), (m, 11H), 2.72 (dd, 1H, J = 12.0 and 4.8 Hz, H-3 ax ), 2.02 (s, 3H), 1.62 (t, 1H, J = 12.0 Hz, H-3 eq ); 13 C NMR (75 MHz, D 2 O) δ , , , , (2C), (2C), , 99.14, 74.23, 73.72, 72.24, 70.63, 70.26, 70.02, 67.98, 67.76, 63.49, 62.83, 52.22, 40.01, 22.27; HRMS (ESI) m/z calcd for C 23 H 31 N 2 O 16 (M-Na) , found
8 Neu5Acα2,3GalβpNP (8) - 7 -
9 Neu5,9Ac 2 α2,3galβpnp (9) - 8 -
10 Neu5Ac9Ltα2,3GalβpNP (10) - 9 -
11 Neu5Gcα2,3GalβpNP (11)
12 KDNα2,3GalβpNP (12)
13 Neu5Acα2,6GalβpNP (13)
14 Neu5,9Ac 2 α2,6galβpnp (14)
15 Neu5Ac9Ltα2,6GalβpNP (15)
16 Neu5Gcα2,6GalβpNP (16)
17 KDNα2,6GalβpNP (17)
18 Neu5Acα2,6GalNAcβpNP (18)
19 Neu5,9Ac 2 α2,6galnacβpnp (19)
20 Neu5Ac9Ltα2,6GalNAcβpNP (20)
21 Neu5Gcα2,6GalNAcβpNP (21)
22 KDNα2,6GalNAcβpNP (22)
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