Beilstein J. Org. Chem. 2017, 13, 164–173.
14.Park, I. H.; Pritchard, D. G.; Cartee, R.; Brandao, A.;
immunological analysis of S. pneumoniae serotype 12F can be
undertaken, and future work will address the expanded inclu-
sion of this antigen in next-generation glycoconjugate vaccines.
Brandileone, M. C. C.; Nahm, M. H. J. Clin. Microbiol. 2007, 45,
15.Heidelberger, M.; Avery, O. T. J. Exp. Med. 1924, 40, 301–316.
Abbreviations
16.Calix, J. J.; Nahm, M. H. J. Infect. Dis. 2010, 202, 29–38.
Ac: acetate ester; BAIB: bis(acetoxy)iodobenzene; Bz: benzoyl;
CPS: capsular polysaccharide; DMF: N,N-dimethylformamide;
EtOAc: ethyl acetate; GlcA: glucouronic acid; HPLC: high-
performance liquid chromatography; Lev: levulinoyl;
MALDI–TOF MS: matrix-assisted laser desorption/
ionization–time of flight mass spectrometry; NAP: 2-naphthyl-
methyl; TBS: tert-butyldimethylsilyl; THF: tetrahydrofuran;
TMSOTf: trimethylsilyl trifluoromethanesulfonate.
17.Robbins, J. B.; Austrian, R.; Lee, C. J.; Rastogi, S. C.; Schiffman, G.;
Henrichsen, J.; Makela, P. H.; Broome, C. V.; Facklam, R. R.;
Tiesjema, R. H.; Parke, J. C. J. Infect. Dis. 1983, 148, 1136–1159.
18.Rodgers, G. L.; Arguedas, A.; Cohen, R.; Dagan, R. Vaccine 2009, 27,
19.Oberli, M. A.; Tamborrini, M.; Tsai, Y.-H.; Werz, D. B.; Horlacher, T.;
Adibekian, A.; Gauss, D.; Möller, H. M.; Pluschke, G.; Seeberger, P. H.
20.Werz, D. B.; Seeberger, P. H. Angew. Chem., Int. Ed. 2005, 44,
Supporting Information
21.Tamborrini, M.; Werz, D. B.; Frey, J.; Pluschke, G.; Seeberger, P. H.
Angew. Chem., Int. Ed. 2006, 45, 6581–6582.
Supporting Information File 1
Experimental details and full characterization data of all
new compounds.
22.Johnson, M. A.; Pinto, B. M. J. Am. Chem. Soc. 2002, 124,
23.Yu, X. H.; Sun, Y.; Frasch, C.; Concepcion, N.; Nahm, M. H.
Clin. Diagn. Lab. Immunol. 1999, 6, 519–524.
24.Codée, J. D. C.; Christina, A. E.; Walvoort, M. T. C.; Overkleeft, H. S.;
van der Marel, G. A. Uronic Acids in Oligosaccharide and
Glycoconjugate Synthesis. In Reactivity Tuning in Oligosaccharide
Assembly; Fraser-Reid, B.; Cristóbal López, J., Eds.; Springer-Verlag:
25.van den Bos, L. J.; Codée, J. D. C.; Litjens, R. E. J. N.; Dinkelaar, J.;
Overkleeft, H. S.; van der Marel, G. A. Eur. J. Org. Chem. 2007,
Acknowledgements
We thank the Max Planck Society and the Körber Foundation
(Award to P.H.S.) for generous financial support and Dr.
Allison Berger for editing the manuscript.
26.Lefeber, D. J.; Kamerling, J. P.; Vliegenthart, J. F. G. Chem. – Eur. J.
2001, 7, 4411–4421.
References
1. Friedländer, C. Fortschr. Med. 1883, 1, 715–733.
2. Pasteur, L. Bull. Acad. Med. (Paris, Fr.) 1881, 10, 94–103.
3. Sternberg, G. M. Nat. Board Health Bull. 1881, 2, 781–783.
4. Musher, D. M. Clin. Infect. Dis. 1992, 14, 801–809.
27.Allevi, P.; Paroni, R.; Ragusa, A.; Anastasia, M.
Tetrahedron: Asymmetry 2004, 15, 3139–3148.
5. O'Brien, K. L.; Wolfson, L. J.; Watt, J. P.; Henkle, E.; Deloria-Knoll, M.;
McCall, N.; Lee, E.; Mulholland, K.; Levine, O. S.; Cherian, T. Lancet
6. Henrichsen, J. J. Clin. Microbiol. 1995, 33, 2759–2762.
7. Lund, E.; Henrichsen, J. Laboratory Diagnosis, Serology and
Epidemiology of Streptococcus pneumoniae. In Methods in
Microbiology; Bergan, T.; Norris, J. R., Eds.; Academic Press, 1978;
Vol. 12, pp 241–262.
28.de Jong, A.-R.; Hagen, B.; van der Ark, V.; Overkleeft, H. S.;
Codée, J. D. C.; van der Marel, G. A. J. Org. Chem. 2012, 77,
29.Polat, T.; Wong, C.-H. J. Am. Chem. Soc. 2007, 129, 12795–12800.
30.Wang, Z.; Xu, Y.; Yang, B.; Tiruchinapally, G.; Sun, B.; Liu, R.;
Dulaney, S.; Liu, J.; Huang, X. Chem. – Eur. J. 2010, 16, 8365–8375.
8. Reeves, R. E.; Goebel, W. E. J. Biol. Chem. 1941, 139, 511–519.
9. Moxon, E. R.; Kroll, J. S. Curr. Top. Microbiol. Immunol. 1990, 150,
31.Wu, X.; Cui, L.; Lipinski, T.; Bundle, D. R. Chem. – Eur. J. 2010, 16,
32.Kramer, S.; Nolting, B.; Ott, A.-J.; Vogel, C. J. Carbohydr. Chem. 2000,
10.Austrian, R. Clin. Infect. Dis. 1981, 3 (Suppl. S1), S1–S17.
33.Daragics, K.; Fügedi, P. Tetrahedron Lett. 2009, 50, 2914–2916.
11.Austrian, R. Clin. Infect. Dis. 1989, 11 (Suppl. S3), S598–S602.
34.Eller, S.; Collot, M.; Yin, J.; Hahm, H. S.; Seeberger, P. H.
Angew. Chem., Int. Ed. 2013, 52, 5858–5861.
12.Committee on Infectious Diseases. Pediatrics 2010, 126, 186–190.
13.Plosker, G. L. Pediatr. Drugs 2013, 15, 403–423.
35.Demchenko, A. V.; Rousson, E.; Boons, G.-J. Tetrahedron Lett. 1999,
172