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Volumn 16, Issue 11, 2010, Pages 3476-3488

Synthesis of monomeric and dimeric repeating units of the zwitterionic type 1 capsular polysaccharide from Streptococcus pneumoniae

(4) Wu, Xiangyang b Cui, Lina c Lipinski, Tomasz a Bundle, David R a

a UNIVERSITY OF ALBERTA (Canada)

b MEMORIAL SLOAN KETTERING CANCER CENTER (United States)

c UNIVERSITY OF CALIFORNIA (United States)

Author keywords

Glycosylation; Oxidation; Polysaccharides; T cell activation; Uronic acid

Indexed keywords

BACTEROIDES FRAGILIS; CAPSULAR POLYSACCHARIDES; CELL ACTIVITY; FULLY PROTECTED; GALACTOSE RESIDUES; GLYCOSYL DONORS; HEXASACCHARIDES; HYDROXYL GROUPS; KEY ELEMENTS; O-ACETYL GROUP; REPEATING UNIT; SELECTIVE DEPROTECTION; STEREOSELECTIVE CONSTRUCTION; STREPTOCOCCUS PNEUMONIAE; SYNTHONS; T CELL ACTIVATION; URONIC ACID; URONIC ACIDS;

ACIDS; CARBOXYLIC ACIDS; ESTERIFICATION; GLUCOSE; GLYCOSYLATION; OXIDATION; POLYSACCHARIDES;

SYNTHESIS (CHEMICAL);

BACTERIAL POLYSACCHARIDE; POLYSACCHARIDE; URONIC ACID;

ARTICLE; BACTERIAL MEMBRANE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; STREPTOCOCCUS PNEUMONIAE; SYNTHESIS;

BACTERIAL CAPSULES; OXIDATION-REDUCTION; POLYSACCHARIDES; POLYSACCHARIDES, BACTERIAL; STEREOISOMERISM; STREPTOCOCCUS PNEUMONIAE; URONIC ACIDS;

EID: 77949303171 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.200902460 Document Type: Article

Times cited : (44)

References (60)

1
- 0002574907
- (Ed. : W. E., Paul) Lippincott-Raven, New York
- a) M. H. Nahm, M. A. Apicella, D. E. Briles, Immunity to Extracellular Bacteria, in Fundamental Immunology (Ed. : W. E., Paul) Lippincott-Raven, New York, 1999, pp. 1373-1386;
- (1999) Immunity to Extracellular Bacteria, in Fundamental Immunology , pp. 1373-1386
- Nahm, M.H.¹ Apicella, M.A.² Briles, D.E.³

2
- 0034030809
- b) L. G. Rubin, Pediatr. Clin. North Am. 2000, 47, 269-285;
- (2000) Pediatr. Clin. North Am. , vol.47 , pp. 269-285
- Rubin, L.G.¹

3
- 0034971094
- c) M. J. Jedrzejas, Microbiol. Mol. Biol. Rev. 2001, 65, 187-207.
- (2001) Microbiol. Mol. Biol. Rev. , vol.65 , pp. 187-207
- Jedrzejas, M.J.¹

4
- 0034629296
- a) A. O. Tzianabos, R. W. Finberg, Y. Wang, M. Chan, A. B. Onderdonk, H. X Jennings, D. L. Kaper, J. Biol. Chem. 2000, 275, 6733-6740;
- (2000) J. Biol. Chem. , vol.275 , pp. 6733-6740
- Tzianabos, A.O.¹ Finberg, R.W.² Wang, Y.³ Chan, M.⁴ Onderdonk, A.B.⁵ Jennings, H.X.⁶ Kaper, D.L.⁷

5
- 0033557733
- b) J. O. Brubaker, Q. Li, A. O. Tzianabos, D. L. Kasper, R. W. Finberg, J. Immunol. 1999, 162, 2235-2242;
- (1999) J. Immunol. , vol.162 , pp. 2235-2242
- Brubaker, J.O.¹ Li, Q.² Tzianabos, A.O.³ Kasper, D.L.⁴ Finberg, R.W.⁵

6
- 0026762857
- c) P. J. Baker, J. Infect. Dis. 1992, 165, S44-S48;
- (1992) J. Infect. Dis. , vol.165
- Baker, P.J.¹

7
- 0032944216
- d) N. M. Zirk, S. F. Hashmi, H. K. Ziegler, Infect. Immun. 1999, 67, 319-326.
- (1999) Infect. Immun. , vol.67 , pp. 319-326
- Zirk, N.M.¹ Hashmi, S.F.² Ziegler, H.K.³

8
- 42449127005
- J. Duan, F. Y. Avci, D. L. Kasper, Proc. Natl. Acad. Sci. USA 2008, 105, 5183-5188.
- (2008) Proc. Natl. Acad. Sci. USA , vol.105 , pp. 5183-5188
- Duan, J.¹ Avci, F.Y.² Kasper, D.L.³

9
- 0027993006
- a) A. O. Tzianabos, A. B. Onderdonk, D. F. Zaleznik, R. S. Smith, D. L. Kasper, Infect. Immun. 1994, 62, 4881-4886;
- (1994) Infect. Immun. , vol.62 , pp. 4881-4886
- Tzianabos, A.O.¹ Onderdonk, A.B.² Zaleznik, D.F.³ Smith, R.S.⁴ Kasper, D.L.⁵

10
- 40049102556
- b) S. Gallorini, F. Berti, P. Parente, R. Baronio, S. Aprea, U. D'Oro, M, Pizza, J. L. Telford, A. Wack, J. Immunol. 2007, 179, 8208-8215.
- (2007) J. Immunol. , vol.179 , pp. 8208-8215
- Gallorini, S.¹ Berti, F.² Parente, P.³ Baronio, R.⁴ Aprea, S.⁵ D'Oro, U.⁶ Pizza, M.⁷ Telford, J.L.⁸ Wack, A.⁹

11
- 0034650488
- W. M. Kalka-Moll, A. O. Tzianabos, Y. Wang, V. J. Carey, R. W. Finberg, A. B. Onderdonk, D. L. Kasper, J. Immunol. 2000, 164, 719-724.
- (2000) J. Immunol. , vol.164 , pp. 719-724
- Kalka-Moll, W.M.¹ Tzianabos, A.O.² Wang, Y.³ Carey, V.J.⁴ Finberg, R.W.⁵ Onderdonk, A.B.⁶ Kasper, D.L.⁷

12
- 0347155584
- Y.-H. Choi, M. H. Roehrl, D. L. Kasper, J. Y. Wang, Biochemistry 2002, 41, 15144-15151.
- (2002) Biochemistry , vol.41 , pp. 15144-15151
- Choi, Y.-H.¹ Roehrl, M.H.² Kasper, D.L.³ Wang, J.Y.⁴

13
- 0035979248
- A. O. Tzianabos, J. Y. Wang, J. C. Lee, Proc. Natl. Acad. Sci. USA 2001, 98, 9365-9370.
- (2001) Proc. Natl. Acad. Sci. USA , vol.98 , pp. 9365-9370
- Tzianabos, A.O.¹ Wang, J.Y.² Lee, J.C.³

14
- 33947111414
- L. J. van den Bos, T. J. Boltje, T. Provoost, J. Mazurek, H. S. Overkleeft, G. A. van der Marel, Tetrahedron Lett. 2007, 48, 2697-2700.
- (2007) Tetrahedron Lett. , vol.48 , pp. 2697-2700
- Van Den Bos, L.J.¹ Boltje, T.J.² Provoost, T.³ Mazurek, J.⁴ Overkleeft, H.S.⁵ Van Der Marel, G.A.⁶

15
- 77949302531
- Ph.D. Thesis, Leiden University (The Netherlands)
- L. J. van den Bos, Ph.D. Thesis, Leiden University (The Netherlands), 2007.
- (2007)
- Van Den Bos, L.J.¹

16
- 27744472923
- a) J.-H. Kim, H. Yang, G.-J. Boons, Angew. Chem. 2005, 117, 969-971;
- (2005) Angew. Chem. , vol.117 , pp. 969-971
- Kim, J.-H.¹ Yang, H.² Boons, G.-J.³

17
- 13744262178
- Angew. Chem. Int. Ed. 2005, 44, 947-949;
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 947-949

18
- 24144498474
- b) J.-H. Kim, H. Yang, J. Park, G.-J. Boons, J. Am. Chem. Soc. 2005, 127, 12090-12097.
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 12090-12097
- Kim, J.-H.¹ Yang, H.² Park, J.³ Boons, G.-J.⁴

19
- 0001508720
- a) Y. Nakahara, T. Ogawa, Tetrahedron Lett. 1987, 28, 2731-2734;
- (1987) Tetrahedron Lett. , vol.28 , pp. 2731-2734
- Nakahara, Y.¹ Ogawa, T.²

20
- 34548132442
- b) L. J. Van. Den Bos, J. D. C. Codee, R. E. J. N. Litjens, J. Dinkelaar, H. S. Overkleeft, G. A. Van der Marcel, Eur. J. Org. Chem. 2007, 3963-3976;
- (2007) Eur. J. Org. Chem. , pp. 3963-3976
- Van Den Bos, L.J.¹ Codee, J.D.C.² Litjens, R.E.J.N.³ Dinkelaar, J.⁴ Overkleeft, H.S.⁵ Van Der Marcel, G.A.⁶

21
- 0034994242
- c) M. Haller, G.-J. Boons, J. Chem. Soc. Perkin Trans. 1 2001, 814-822.
- (2001) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 814-822
- Haller, M.¹ Boons, G.-J.²

22
- 0021485528
- a) H. Lönn, J. Lonngren, J. Carbohydr. Chem. 1984, 132, 39-44;
- (1984) J. Carbohydr. Chem. , vol.132 , pp. 39-44
- Lönn, H.¹ Lonngren, J.²

23
- 0027512468
- b) N. J. Davis, S. L. Flitsch, Tetrahedron Lett. 1993, 34, 1181-1184.
- (1993) Tetrahedron Lett. , vol.34 , pp. 1181-1184
- Davis, N.J.¹ Flitsch, S.L.²

24
- 2142817104
- J. Madaj, M. Jankowska, A. Wiśniewski, Carbohydr. Res. 2004, 339, 1293-1300.
- (2004) Carbohydr. Res. , vol.339 , pp. 1293-1300
- Madaj, J.¹ Jankowska, M.² Wiśniewski, A.³

25
- 0342936076
- K.-H. Jung, M. Müller, R. R. Schmidt, Chem. Rev. 2000, 100, 4423-4442.
- (2000) Chem. Rev. , vol.100 , pp. 4423-4442
- Jung, K.-H.¹ Müller, M.² Schmidt, R.R.³

26
- 24144498474
- J.-H. Kim, H. Yang, J. Park, G.-J. Boons, J. Am. Chem. Soc. 2005, 127, 12090-12097.
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 12090-12097
- Kim, J.-H.¹ Yang, H.² Park, J.³ Boons, G.-J.⁴

27
- 27744472923
- J.-H. Kim, H. Yang, G.-J. Boons, Angew. Chem. 2005, 117, 969-971;
- (2005) Angew. Chem. , vol.117 , pp. 969-971
- Kim, J.-H.¹ Yang, H.² Boons, G.-J.³

28
- 13744262178
- Angew. Chem. Int. Ed. 2005, 44, 947-949.
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 947-949

29
- 0000776112
- a) H. Paulsen, C. Kolar, W Stenzel, Chem. Ber. 1978, 111, 2358-2369;
- (1978) Chem. Ber. , vol.111 , pp. 2358-2369
- Paulsen, H.¹ Kolar, C.² Stenzel, W.³

30
- 0000205069
- b) R. U. Lemieux, R. M. Lemieux, Can. J. Chem. 1979, 57, 1244-1251;
- (1979) Can. J. Chem. , vol.57 , pp. 1244-1251
- Lemieux, R.U.¹ Lemieux, R.M.²

31
- 0000198772
- c) For review of synthesis of oligosaccharide of 2-amino-2-deoxy sugars: J. Banoub, P. Boullanger, D. Lafont, Chem. Rev. 1992, 92, 1167-1195.
- (1992) Chem. Rev. , vol.92 , pp. 1167-1195
- Banoub, J.¹ Boullanger, P.² Lafont, D.³

32
- 33747799654
- S. Manabe, K. Ishii, Y. Ito, J. Am. Chem. Soc. 2006, 128, 10666-10667.
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 10666-10667
- Manabe, S.¹ Ishii, K.² Ito, Y.³

33
- 56449107513
- a) D. Crich, T. Hu, F. Cai, J. Org. Chem. 2008, 73, 8942-8953;
- (2008) J. Org. Chem. , vol.73 , pp. 8942-8953
- Crich, D.¹ Hu, T.² Cai, F.³

34
- 0037152265
- b) Y.-P. Cheng, H.-T. Chen, C.-C. Lin, Tetrahedron Lett. 2002, 43, 7721-7723;
- (2002) Tetrahedron Lett. , vol.43 , pp. 7721-7723
- Cheng, Y.-P.¹ Chen, H.-T.² Lin, C.-C.³

35
- 0033520244
- c) A. V. Demchenko, E. Rousson, G.-J. Boons, Tetrahedron Lett. 1999, 40, 6523-6526.
- (1999) Tetrahedron Lett. , vol.40 , pp. 6523-6526
- Demchenko, A.V.¹ Rousson, E.² Boons, G.-J.³

36
- 77949307828
- Ph.D. Thesis, Konstanz University (Germany)
- a) A. Stadelmaier, Ph.D. Thesis, Konstanz University (Germany), 2003;
- (2003)
- Stadelmaier, A.¹

37
- 84985257207
- b) G. Grundler, R. R. Schmidt, Liebigs Ann. Chem. 1984, 1826-1847.
- (1984) Liebigs Ann. Chem. , pp. 1826-1847
- Grundler, G.¹ Schmidt, R.R.²

38
- 0032576812
- L. Jiang, T.-H. Chan, Tetrahedron Lett. 1998, 39, 355-358.
- (1998) Tetrahedron Lett. , vol.39 , pp. 355-358
- Jiang, L.¹ Chan, T.-H.²

39
- 0012921731
- R. V. Stick, D. Tilbrook, G. Mattew, Aust. J. Chem. 1990, 43, 1643-1655.
- (1990) Aust. J. Chem. , vol.43 , pp. 1643-1655
- Stick, R.V.¹ Tilbrook, D.² Mattew, G.³

40
- 0030593609
- P. B. Alper, S.-C. Hung, C.-H. Wong, Tetrahedron Lett. 1996, 37, 6029-6032.
- (1996) Tetrahedron Lett. , vol.37 , pp. 6029-6032
- Alper, P.B.¹ Hung, S.-C.² Wong, C.-H.³

41
- 0035190661
- M. Grathwohl, R. R. Schmidt, Synthesis 2001, 2263-2272.
- (2001) Synthesis , pp. 2263-2272
- Grathwohl, M.¹ Schmidt, R.R.²

42
- 0033757344
- a) M. V. Chiesa, R. R. Schmidt, Eur. J. Org. Chem. 2000, 3541-3554;
- (2000) Eur. J. Org. Chem. , pp. 3541-3554
- Chiesa, M.V.¹ Schmidt, R.R.²

43
- 0011244207
- b) K. C. Nicolaou, C. A. Veale, C.-K. Hwang, J. Hutchinson, C. V. C. Prasad, W. W. Ogilvie, Angew. Chem. 1991, 103, 304-308;
- (1991) Angew. Chem. , vol.103 , pp. 304-308
- Nicolaou, K.C.¹ Veale, C.A.² Hwang, C.-K.³ Hutchinson, J.⁴ Prasad, C.V.C.⁵ Ogilvie, W.W.⁶

44
- 0025980596
- Angew. Chem. Int. Ed. Engl. 1991, 30, 299-303.
- (1991) Angew. Chem. Int. Ed. Engl. , vol.30 , pp. 299-303

45
- 0030462737
- A. B. Smith III, G. R. Ott, J. Am. Chem. Soc. 1996, 118, 13095-13096.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 13095-13096
- Smith III, A.B.¹ Ott, G.R.²

46
- 0000815238
- a) R. R. Schmidt, Angew. Chem. 1986, 98, 213-236;
- (1986) Angew. Chem. , vol.98 , pp. 213-236
- Schmidt, R.R.¹

47
- 0022636075
- Angew. Chem. Int. Ed. Engl. 1986, 25, 212-235;
- (1986) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 212-235

48
- 0028186224
- b) R. R. Schmidt, W. Kinzy, Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-123.
- (1994) Adv. Carbohydr. Chem. Biochem. , vol.50 , pp. 21-123
- Schmidt, R.R.¹ Kinzy, W.²

49
- 0001157412
- E. Petrakova, U. Spohr, R. U. Lemieux, Can. J. Chem. 1992, 70, 233-240.
- (1992) Can. J. Chem. , vol.70 , pp. 233-240
- Petrakova, E.¹ Spohr, U.² Lemieux, R.U.³

50
- 0027729344
- B. Liessem, A. Giannis, K. Sandhoff, M. Nieger, Carbohydr. Res. 1993, 250, 19-30.
- (1993) Carbohydr. Res. , vol.250 , pp. 19-30
- Liessem, B.¹ Giannis, A.² Sandhoff, K.³ Nieger, M.⁴

51
- 0346434113
- J. Xue, Z. Guo, J. Am. Chem. Soc. 2003, 125, 16334-16339.
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 16334-16339
- Xue, J.¹ Guo, Z.²

52
- 37849189010
- P. J. Garegg, Adv. Carbohydr. Chem. Biochem. 1997, 52, 179-205.
- (1997) Adv. Carbohydr. Chem. Biochem. , vol.52 , pp. 179-205
- Garegg, P.J.¹

53
- 4244144203
- K. Bock, C.J. Pedersen, J. Chem. Soc. Perkin Trans. 1 1974, 2, 293-297.
- (1974) J. Chem. Soc. Perkin Trans. 1 , vol.2 , pp. 293-297
- Bock, K.¹ Pedersen, C.J.²

54
- 0000688610
- T. Sato, J. Otera, H. Nozaki, J. Org. Chem. 1992, 57, 2166-2169.
- (1992) J. Org. Chem. , vol.57 , pp. 2166-2169
- Sato, T.¹ Otera, J.² Nozaki, H.³

55
- 33745897624
- L. Huang, N. Teumelsan, X. Huang, Chem. Eur. J. 2006, 12, 5246-5252.
- (2006) Chem. Eur. J. , vol.12 , pp. 5246-5252
- Huang, L.¹ Teumelsan, N.² Huang, X.³

56
- 0025159938
- a) P. L. Barili, G. Berti, D. Bertozzi, G. Catelani, F. Colonna, T. Corsetti, F. D'Andrea, Tetrahedron 1990, 46, 5365-5376;
- (1990) Tetrahedron , vol.46 , pp. 5365-5376
- Barili, P.L.¹ Berti, G.² Bertozzi, D.³ Catelani, G.⁴ Colonna, F.⁵ Corsetti, T.⁶ D'Andrea, F.⁷

57
- 34047267010
- b) H. M. Branderhorst, R. J. Liskamp, R. J. Pieters, Tetrahedron 2007, 63, 4290-4296.
- (2007) Tetrahedron , vol.63 , pp. 4290-4296
- Branderhorst, H.M.¹ Liskamp, R.J.² Pieters, R.J.³

58
- 0021458804
- P. J. Garegg, Pure. Appl. Chem. 1984, 56, 845-858.
- (1984) Pure. Appl. Chem. , vol.56 , pp. 845-858
- Garegg, P.J.¹

59
- 61849101424
- T. A. Boebel, D. Y. Gin, Angew. Chem. 2003, 115, 6054-6057;
- (2003) Angew. Chem. , vol.115 , pp. 6054-6057
- Boebel, T.A.¹ Gin, D.Y.²

60
- 0347419517
- Angew. Chem. Int. Ed. 2003, 42, 5874-5877.
- (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 5874-5877

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