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(e) Mukhopadhyay, B.; Martins, M. B.; Karamanska, R.; Russell, D. A.; Field, R. A.
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References and notes
1. (a) Paton, J. C.; Paton, A. W. Clin. Microbiol. Rev. 1998, 11, 450–479; (b) Karch,
H.; Tarr, P. I.; Blelaszewska, M. Int. J. Med. Microbiol. 2005, 295, 405–418.
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3. Lacy, D. B.; Stevens, R. C. Curr. Opin. Struct. Biol. 1998, 8, 778–784.
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Biochem. 1988, 171, 45–50.
5. Nyholm, P.-G.; Magnusson, G.; Zheng, Z.; Norel, R.; Binnington-Boyd, B.;
Lingwood, C. A. Chem. Biol. 1996, 3, 263–275.
6. (a) Shimizu, H.; Field, R. A.; Homans, S. W.; Donohue-Rolfe, A. Biochemistry
1998, 31, 11078–11082; (b) Thompson, G. S.; Shimizu, H.; Homans, S. W.;
Donohue-Rolfe, A. Biochemistry 2000, 39, 13153–13156; (c) Shimizu, H.; Brown,
J. M.; Homans, S. W.; Field, R. A. Tetrahedron 1998, 54, 9489–9506.
14. For example, in the generation of carbohydrate microarrays via biotinylation
(Karamanska, R.; Clarke, J.; Blixt, O.; MacRae, J. I.; Zhang, J. Q.; Crocker, P. R.;
Laurent, N.; Wright, A.; Flitsch, S. L.; Russell, D. A.; Field, R. A. Glycoconjugate J.
2008, 25, 69–74) or via amide coupling to self-assembled monolayers (Zhi, Z.-
L.; Laurent, N.; Powell, A. K.; Karamanska, R.; Fais, M.; Voglmeir, J.; Wright, A.;
Blackburn, J. M.; Crocker, P. R.; Russell, D. A.; Flitsch, S. L.; Field, R. A.; Turnbull,
J. E. ChemBioChem 2008, 9, 1568–1575.).
15. Reviewed in: (a) Fairbanks, A. J. Synlett 2003, 1945–1958; (b) Cumpstey, I.
Carbohydr. Res. 2008, 343, 1553–1573.
16. Dan, A.; Ito, Y.; Ogawa, T. J. Org. Chem. 1995, 60, 4680–4681.
17. Pozsgay, V.; Jennings, H. J. Carbohydr. Res. 1988, 179, 61–76.
7. Soltyk, A. M.; MacKenzie, C. R.; Wolski, V. M.; Hirama, T.; Kitov, P. I.; Bundle, D.
R.; Brunton, J. L. J. Biol. Chem. 2002, 277, 5351–5359.
8. Kitov, P. I.; Sadowska, J. M.; Mulvey, G.; Armstrong, G. D.; Ling, H.; Pannu, N. S.;
Read, R. J.; Bundle, D. R. Nature 2000, 403, 669–672.
18. All synthetic intermediates gave combustion analysis or high resolution mass
spectrometry data consistent with their proposed structures. Selected
analytical data for key compounds are as follows:
3-Azidopropyl p-methoxybenzyl ether (5): Colourless liquid, bp 180–185 °C; Rf
0.43 (hexane/EtOAc 9:1); dH (250 MHz, CDCl3): d 1.90 (m, 2H, CH2), 3.44 (t, 2H,
J 6.7 Hz, spacer CH2), 3.57 (t, 2H, J 6.0 Hz, spacer CH2), 3.34 (s, 3H, CH3O), 4.48
(s, 2H, ArCH2O), 6.93 (d, 2H, J 8.7 Hz, aromatic H), 7.30 (d, 2H, J 8.7 Hz, aromatic
H); dC (62.9 MHz, CDCl3): d 29.2 (CH2CH2CH2), 48.5 (CH2N3), 55.2 (CH3O), 66.5
(CH2CH2O), 72.7 (ArCH2O), 113.7, 129.2, 130.2, 159.2 (aromatic C). Anal. Calcd
for C15H11N3O2: C, 59.71; H, 6.83; N, 18.99. Found: C, 59.70; H, 6.80; N, 19.30.
9. For instance: (a) Lundquist, J. J.; Debenham, S. D.; Toone, E. J. J. Org. Chem. 2000,
65, 8245–8250; (b) Nishikawa, K.; Matsuoka, K.; Kita, E.; Okabe, N.; Mizuguchi,
M.; Hino, K.; Miyazawa, S.; Yamasaki, C.; Aoki, J.; Takashima, S.; Yamakawa, Y.;
Nishijima, M.; Terunuma, D.; Kuzuhara, H.; Natori, Y. Proc. Natl. Acad. Sci. U.S.A.
2002, 99, 7669–7674; (c) Watanabe, M.; Igai, K.; Matsuoka, K.; Miyagawa, A.;
Watanabe, T.; Yanoshita, R.; Samejima, Y.; Terunuma, D.; Natori, Y.; Nishikawa,
K. Infect. Immun. 2006, 74, 1984–1988; (d) Isobe, H.; Cho, K.; Solin, N.; Werz, D.
B.; Seeberger, P. H.; Nakamura, E. Org. Lett. 2007, 9, 4611–4614; (e) Neri, P.;
Tokoro, S.; Yokoyama, S.; Miura, T.; Murata, T.; Nishida, Y.; Kajimoto, T.;
Tsujino, S.; Inazu, T.; Usui, T.; Mori, H. Biol. Pharm. Bull. 2007, 30, 1697–1701.
10. For instance: (a) Armstrong, G. D.; Rowe, P. C.; Orrbine, E.; Klassen, T. P.; Wells,
G.; Mackenzie, A.; Lior, H.; Blanchard, C.; Auclair, F.; Thompson, B.; Rafter, D. J.;
McLaine, P. N. J. Infect. Dis. 1995, 171, 1042–1045; (b) Paton, A. W.; Morona, R.;
Paton, J. C. Nat. Med. 2000, 6, 265–270; (c) Mulvey, G. L.; Marcato, P.; Kitov, P. I.;
Sadowska, J.; Bundle, D. R.; Armstrong, G. D. J. Infect. Dis. 2003, 187, 640–649.
11. Kitov, P. I.; Mulvey, G. L.; Griener, T. P.; Lipinski, T.; Solomon, D.; Paszkiewicza,
E.; Jacobson, J. M.; Sadowska, J. M.; Suzuki, M.; Yamamura, K. I.; Armstrong, G.
D.; Bundle, D. R. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 16837–16842.
12. For instance: (a) Goldman, E. R.; Clapp, A. R.; Anderson, G. P.; Uyeda, H. T.; Mauro,
J. M.; Medintz, I. L.; Mattoussi, H. Anal. Chem. 2004, 76, 684–688; (b) Uzawa, H.;
Ito, H.; Neri, P.; Mori, H.; Nishida, Y. ChemBioChem 2007, 8, 2117–2124; (c) Chien,
Y. Y.; Jan, M. D.; Adak, A. K.; Tzeng, H. C.; Lin, Y. P.; Chen, Y. J.; Wang, K. T.; Chen, C.
T.; Chen, C. C.; Lin, C. C. ChemBioChem 2008, 9, 1100–1109; (d) Kale, R. R.;
McGannon, C. M.; Fuller-Schaefer, C.; Hatch, D. M.; Flagler, M. J.; Gamage, S. D.;
Weiss, A. A.; Iyer, S. S. Angew. Chem., Int. Ed. 2008, 47, 1265–1268.
3-Azidopropyl
(2-amino-2-deoxy-b-
D-galactopyranosyl)-(1?3)-a-D-galactopy-
ranoside (1):
[
a
]
+137 (c 0.3, H2O); Rf 0.53 (EtOAc/HOAc/MeOH/H2O
D
0
0
0
5:3:3:2); dH (500 MHz, D2O) 2.02 (m, 2H, spacer-CH2), 3.02 (dd, 1H, J1 ,2
8 Hz, J2 ,3 10 Hz, H20), 3.56 (m, 2H, spacer-CH2N3), 3.66 (dd, 1H, J2 ,3 10 Hz, J3 ,4
0
0
0
0
0
3 Hz, H30), 3.69 (m, 1H, spacer-CH2O), 3.76 (dd, 1H, J5 ,6 a 4 Hz, J5 ,6 b 7 Hz, H50),
0
0
0
0
3.82–3.87 (m, 4H, H6a, H6b, H60a, H60b), 3.91 (m, 1H, spacer-CH2O), 3.95 (m,
1H, H4), 4.07 (m, 3H, H2, H3, H5), 4.34 (m, 1H, H40), 4.61 (d, 1H, J1 ,2 8 Hz, H10),
5.05 (d, 1H, J1,2 4 Hz, H1); dC (D2O) 28.8 (CH2CH2CH2), 49.0 (CH2N3), 54.0 (C20),
61.9 (2 ꢀ C; C6, C60), 65.8 (CH2CH2O), 68.0 (C2), 68.6 (C40), 70.0 (C4), 71.4 (C5),
73.5 (C30), 76.0 (C50), 80.5 (C3), 99.1 (C1), 105.9 (C10); ESI-MS calcd for
C15H28N4O10 424.18, m/z 447.17 [M+Na]+.
0
0
3-Azidopropyl (2-acetamido-2-deoxy-b-
ranoside (2): [ D +110 (c 0.18, H2O); Rf 0.68 (EtOAc/HOAc/MeOH/H2O 5:3:3:2);
dH (500 MHz, D2O) 2.01 (m, 2H, spacer-CH2), 2.12 (s, 3H, NHAc), 3.55 (m, 2H,
D-galactopyranosyl)-(1,3)-a-D-galactopy-
a
]
0
0
0
0
spacer-CH2N3), 3.67 (m, 1 H, spacer-CH2O), 3.75 (dd, 1H, J5 ,6 a 4 Hz, J5 ,6 b 8 Hz,
H50), 3.80–3.86 (m, 5H, H30, H6a, H6b, H60a, H60b), 3.89 (m, 1H, spacer-CH2O),
3.96 (dd, 1H, J1,2 4 Hz, J2,3 10 Hz, H2), 4.00 (dd, 1H, J2,3 10 Hz, J3,4 2 Hz, H3), 4.01
(m, 3H, H5, H20, H40), 4.28 (m, 1H, H4), 4.72 (d, 1H, J1 ,2 8 Hz, H10), 5.00 (d, 1H,
J1,2 4 Hz, H1); dC (D2O) 23.1 (CH3CON), 28.8 (CH2CH2CH2), 49.1 (CH2N3), 53.5
(C20), 61.9 and 62.0 (C6, C60), 65.9 (CH2CH2O), 68.2 (C2), 68.6 (C40), 70.1 (C4),
71.4 (C5), 71.7 (C30), 75.8 (C50), 79.9 (C3), 99.4 (C1), 104.1 (C10), 176.1
(CH3CON); ESI-MS calcd for C17H30N4O11 466.19, m/z 489.2 [M+Na]+.
19. Hasegawa, A.; Nagahama, T.; Ohki, H.; Kiso, M. J. Carbohydr. Chem. 1992, 11,
699–714.
0
0
13. Thioctic acid amide tethers for achieving low non-specific protein binding to
gold glyconanoparticles. (a) Karamanska, R.; Mukhopadhyay, B.; Russell, D. A.;
Field, R. A. Chem. Commun. 2005, 3334–3336; Silver and gold glyconanoparticles
for colorimetric bioassays. (b) Schofield, C. L.; Haines, A. H.; Field, R. A.; Russell, D.
A. Langmuir 2006, 22, 6707–6711; Glyconanoparticles for the colorimetric
detection of cholera toxin: (c) Schofield, C. L.; Field, R. A.; Russell, D. A. Anal. Chem.
2007, 79, 1356–1361; Detection of Ricinus communis agglutinin 120 using
carbohydrate-stabilised gold nanoparticles. (d) Schofield, C. L.; Mukhopadhyay,
20. Kanie, O.; Crawley, S. C.; Palcic, M. M.; Hindsgaul, O. Carbohydr. Res. 1993, 243,
139–164.