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Angewandte Chemie - International Edition

Volumn 49, Issue 14, 2010, Pages 2585-2590

Total synthesis of lipoteichoic acid of streptococcus pneumoniae

(6) Pedersen, Christian Marcus a Figueroa Perez, Ignacio a Lindner, Buko b Ulmer, Artur J b Zähringer, Ulrich b Schmidt, Richard R a,b

a UNIVERSITY OF KONSTANZ (Germany)

b RESEARCH CENTER BORSTEL (Germany)

Author keywords

Cram positive bacteria; Cytokines; Glycolipids; Glycosylation; Total synthesis

Indexed keywords

CHEMICAL EQUATIONS; CYTOKINES; GLUCOSE RESIDUES; GLYCOLIPIDS; IMMUNE SYSTEMS; LIPOTEICHOIC ACIDS; MIXED SIGNAL; SIGNALING RECEPTOR; STREPTOCOCCUS PNEUMONIAE; SUGAR UNITS; TOTAL SYNTHESIS;

BACTERIOLOGY; ESTERIFICATION; GLUCOSE; GLYCOSYLATION; LIPIDS; SUGAR (SUCROSE);

SYNTHESIS (CHEMICAL);

LIPOPOLYSACCHARIDE; LIPOTEICHOIC ACID; TEICHOIC ACID;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; HUMAN; MOLECULAR GENETICS; STREPTOCOCCUS PNEUMONIAE; SYNTHESIS;

CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; HUMANS; LIPOPOLYSACCHARIDES; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; STREPTOCOCCUS PNEUMONIAE; TEICHOIC ACIDS;

EID: 77950226522 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.200906163 Document Type: Article

Times cited : (50)

References (53)

1
- 0029816056
- K. M. Zangwill, C. M. Vadheim, A. M. Vannier, L. S. Hemenway, P. D. Greenberg, J. I. Ward, J. Infect. Dis. 1996, 174, 752-759.
- (1996) J. Infect. Dis. , vol.174 , pp. 752-759
- Zangwill, K.M.¹ Vadheim, C.M.² Vannier, A.M.³ Hemenway, L.S.⁴ Greenberg, P.D.⁵ Ward, J.I.⁶

2
- 0034971094
- 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

3
- 0032551901
- F. D. Lowy, N. Engl. J. Med. 1998, 339, 520-532.
- (1998) N. Engl. J. Med. , vol.339 , pp. 520-532
- Lowy, F.D.¹

4
- 0027181992
- W. Fischer, T Behr, R. Hartmann, J. Peter-Katalinic, H. Egge, Eur. J. Biochem. 1993, 215, 851-857;
- (1993) Eur. J. Biochem. , vol.215 , pp. 851-857
- Fischer, W.¹ Behr, T.² Hartmann, R.³ Peter-Katalinic, J.⁴ Egge, H.⁵

5
- 0030017520
- J.W. Greenberg, W. Fischer, K. A. Jonier, Infect. Immun. 1996, 64, 3318-3325;
- (1996) Infect. Immun. , vol.64 , pp. 3318-3325
- Greenberg, J.W.¹ Fischer, W.² Jonier, K.A.³

6
- 0031415055
- W. Fischer, Microb. Drug Resist. 1997, 3, 309-325.
- (1997) Microb. Drug Resist. , vol.3 , pp. 309-325
- Fischer, W.¹

7
- 41549141383
- This division into lipid anchor and repeating unit was introduced by Fischer et al.. ref. [4]. Recently a different division between lipid anchor and repeating unit was proposed: H. S. Seo, R. T. Cartree, D. G. Pritchard, M. H. Nahm, J. Bacteriol. 2008, 190, 2379-2387.
- (2008) J. Bacteriol. , vol.190 , pp. 2379-2387
- Seo, H.S.¹ Cartree, R.T.² Pritchard, D.G.³ Nahm, M.H.⁴

8
- 13444280215
- K. Hoebe, P. Georgel, S. Rutschmann, X. Du, S. Mudd, K. Crozat, S. Sovath. L. Shamel, T. Hartung, U. Zähringer, B. Beutle, Nature 2005, 433, 523-527;
- (2005) Nature , vol.433 , pp. 523-527
- Hoebe, K.¹ Georgel, P.² Rutschmann, S.³ Du, X.⁴ Mudd, S.⁵ Crozat, K.⁶ Sovath, S.⁷ Shamel, L.⁸ Hartung, T.⁹ Zähringer, U.¹⁰ Beutle, B.¹¹

9
- 0012917346
- A. Stadelmaier, S. Morath,T. Hartung, R. R. Schmidt, Angew. Chem. 2003, 115, 945-949;
- (2003) Angew. Chem. , vol.115 , pp. 945-949
- Stadelmaier, A.¹ Morath, S.² Hartung, T.³ Schmidt, R.R.⁴

10
- 0242586018
- Angew. Chem. Int. Ed. 2003, 42, 916-920;
- (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 916-920

11
- 0141446169
- S. H. Han, J. K. Kim, M. Martin, S. M. Michalek, M. H. Nahm, Infect. Immun. 2003, 71, 5541-5548.
- (2003) Infect. Immun. , vol.71 , pp. 5541-5548
- Han, S.H.¹ Kim, J.K.² Martin, M.³ Michalek, S.M.⁴ Nahm, M.H.⁵

12
- 0038182550
- N.W. Schröder, S. Morath, C. Alexander, L. Hamann, T. Hartung, U. Zähringer, U. B. Göbel, J. R. Weber. R. R. Schumann, J. Biol. Chem. 2003, 278, 15587-15594.
- (2003) J. Biol. Chem. , vol.278 , pp. 15587-15594
- Schröder, N.W.¹ Morath, S.² Alexander, C.³ Hamann, L.⁴ Hartung, T.⁵ Zähringer, U.⁶ Göbel, U.B.⁷ Weber, J.R.⁸ Schumann, R.R.⁹

13
- 41649115159
- U. Zähringer, B. Lindner, S. Inamura, H. Heine, C Alexander, Immunobiology 2008, 213, 205-224.
- (2008) Immunobiology , vol.213 , pp. 205-224
- Zähringer, U.¹ Lindner, B.² Inamura, S.³ Heine, H.⁴ Alexander, C.⁵

14
- 66149125243
- K. Tawaratsumida, M. Furuyashiki, Y. Fujimoto, K. Fukase, Y. Suda, M. Hashimoto. J. Biol. Chem. 2009, 284, 9147-9152;
- (2009) J. Biol. Chem. , vol.284 , pp. 9147-9152
- Tawaratsumida, K.¹ Furuyashiki, M.² Fujimoto, Y.³ Fukase, K.⁴ Suda, Y.⁵ Hashimoto, M.⁶

15
- 33847370642
- M. Hashimoto, M. Furuyashiki, Y. Suda, J. Immunol. 2007, 178, 2610-2611;
- (2007) J. Immunol. , vol.178 , pp. 2610-2611
- Hashimoto, M.¹ Furuyashiki, M.² Suda, Y.³

16
- 33747806614
- M. Hashimoto, K. Tawaratsumida, H. Kariya, A. Kiyohara, Y. Suda, F. Kirikae, T. Kirikae, F. Götz, J. Immunol. 2006, 177, 3162-3169.
- (2006) J. Immunol. , vol.177 , pp. 3162-3169
- Hashimoto, M.¹ Tawaratsumida, K.² Kariya, H.³ Kiyohara, A.⁴ Suda, Y.⁵ Kirikae, F.⁶ Kirikae, T.⁷ Götz, F.⁸

17
- 33847361765
- S. von Aulock, T. Härtung, C Hermann, J. Immunol. 2007, 178, 2610.
- (2007) J. Immunol. , vol.178 , pp. 2610
- Von Aulock, S.¹ Härtung, T.² Hermann, C.³

18
- 67649763474
- K. Kurokawa, H. Lee, K.-B. Roh, M. Asanuma, Y. S. Kim, H. Nakayama, A. Shiatsuchi, Y. Choi. O. Takenchi. H. J. Kang. N. Dohmae, Y. Nakanishi, S. Akira, K. Sekimizu, B. L. Lee, J. Biol. Chem. 2009, 284, 8406-8411.
- (2009) J. Biol. Chem. , vol.284 , pp. 8406-8411
- Kurokawa, K.¹ Lee, H.² Roh, K.-B.³ Asanuma, M.⁴ Kim, Y.S.⁵ Nakayama, H.⁶ Shiatsuchi, A.⁷ Choi, Y.⁸ Takenchi, O.⁹ Kang, H.J.¹⁰ Dohmae, N.¹¹ Nakanishi, Y.¹² Akira, S.¹³ Sekimizu, K.¹⁴ Lee, B.L.¹⁵

19
- 11144334092
- S. Vialle, P. Sepulcri, J. Dubayle, P. Talaga, Carbohydr. Res. 2005, 340, 91-96.
- (2005) Carbohydr. Res. , vol.340 , pp. 91-96
- Vialle, S.¹ Sepulcri, P.² Dubayle, J.³ Talaga, P.⁴

20
- 33845930022
- C. Draing, M. Pfitzenmaier. S. Zummo. G. Mancuso. A. Geyer, T. Hartung, S. von Aulock, J. Biol. Chem. 2006, 281, 33849-33859.
- (2006) J. Biol. Chem. , vol.281 , pp. 33849-33859
- Draing, C.¹ Pfitzenmaier S Zummo G Mancuso A Geyer, M.² Hartung, T.³ Von Aulock, S.⁴

21
- 33748670479
- M. Kovacs, A. Halfmann. I. Fedtke. M. Heintz, A. Peschel. W. Vollmer. R. Hakenbeck, R. Bruckner. J. Bacteriol. 2006, 188, 5797-5805.
- (2006) J. Bacteriol. , vol.188 , pp. 5797-5805
- Kovacs, M.¹ Halfmann, A.² Fedtke, I.³ Heintz, M.⁴ Peschel, A.⁵ Vollmer, W.⁶ Hakenbeck, R.⁷ Bruckner, R.⁸

22
- 0000815238
- R. R. Schmidt, Angew. Chem. 1986, 98, 213-236;
- (1986) Angew. Chem. , vol.98 , pp. 213-236
- Schmidt, R.R.¹

23
- 0022636075
- Angew. Chem. Int. Ed. Engl. 1986, 25, 212-235;
- (1986) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 212-235

24
- 0028186224
- 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

25
- 66749158101
- X. Zhu, R. R. Schmidt, Angew. Chem. 2009, 121, 1932-1967;
- (2009) Angew. Chem. , vol.121 , pp. 1932-1967
- Zhu, X.¹ Schmidt, R.R.²

26
- 61849111654
- Angew. Chem. Int. Ed. 2009, 48, 1900-1934.
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 1900-1934

27
- 0001348316
- P. Smid, M. de Zwart, W. P. A. Jörning, G. A. van der Marel, J. H. van Boom, J. Carbohydr. Chem. 1993, 12, 1073-1090;
- (1993) J. Carbohydr. Chem. , vol.12 , pp. 1073-1090
- Smid, P.¹ De Zwart, M.² Jörning, W.P.A.³ Van Der Marel, G.A.⁴ Van Boom, J.H.⁵

28
- 33746749929
- H. Liang, T. B. Grindley, J. Carbohydr. Chem. 2004, 23, 71-82;
- (2004) J. Carbohydr. Chem. , vol.23 , pp. 71-82
- Liang, H.¹ Grindley, T.B.²

29
- 77950235068
- and references therein.
- L. J. van den Bos, T. J. Boltje, T. Provoest, J. Mazurek, H. S. Overkleeft. G.A. van der Marel. Tetrahedron Lett. 2007, 48, 2967-2970, and references therein.
- (2007) Tetrahedron Lett. , vol.48 , pp. 2967-2970
- Van Den Bos, L.J.¹ Boltje, T.J.² Provoest, T.³ Mazurek, J.⁴ Overkleeft, H.S.⁵ Van Der Marel, G.A.⁶

30
- 85022505463
- C. M. Pedersen. I. Figueroa-Perez. J. Boruwa. B. Lindner. U. Zähringer, R. R. Schmidt, manuscript in preparation.
- Manuscript in Preparation
- Pedersen, C.M.¹ Figueroa-Perez, I.² Boruwa, J.³ Lindner, B.⁴ Zähringer, U.⁵ Schmidt, R.R.⁶

31
- 77950211396
- R. Yan, F. Wang, Y. Wu, L. Zhang, X. Ye, Tetrahedron Lett. 2005, 46, 8991-8995.
- (2005) Tetrahedron Lett. , vol.46 , pp. 8991-8995
- Yan, R.¹ Wang, F.² Wu, Y.³ Zhang, L.⁴ Ye, X.⁵

32
- 85047680897
- H. Qui. T. B. Grindley. Can. J. Chem. 1999, 77. 481-494.
- (1999) Can. J. Chem. , vol.77 , pp. 481-494
- Qui, H.¹ Grindley, T.B.²

33
- 70349759635
- S. D. Markad, R. R. Schmidt, Eur. J. Org. Chem. 2009, 5002-5011;
- (2009) Eur. J. Org. Chem. , pp. 5002-5011
- Markad, S.D.¹ Schmidt, R.R.²

34
- 0030881595
- A. K. Sarkar, K. S. Rostand, R. K. Jain, K. L. Matta, J. D. Esko, J. Biol. Chem. 1997, 272, 25608.
- (1997) J. Biol. Chem. , vol.272 , pp. 25608
- Sarkar, A.K.¹ Rostand, K.S.² Jain, R.K.³ Matta, K.L.⁴ Esko, J.D.⁵

35
- 0001763001
- R. R. Schmidt, E. Rücker, Tetrahedron Lett. 1980, 21, 1421-1424:
- (1980) , vol.21 , pp. 1421-1424
- Schmidt, R.R.¹ Rücker, E.² Lett, T.³

36
- 84988126671
- R. R. Schmidt, M. Behrendt, A. Toepfer. Synlett 1990, 694-697.
- (1990) Synlett , pp. 694-697
- Schmidt, R.R.¹ Behrendt, M.² Toepfer, A.³

37
- 13344291142
- A. H. Andreotti, D. Kahne. J. Am. Chem. Soc. 1993, 115, 3352-3353.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 3352-3353
- Andreotti, A.H.¹ Kahne, D.²

38
- 0028097126
- J. A. Ragan, K. Cooper, Bioorg. Med. Chem. Lett. 1994, 4, 2563-2566.
- (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 2563-2566
- Ragan, J.A.¹ Cooper, K.²

39
- 37049130347
- P. A. Gent, R. Gigg, J. Chem. Soc. Perkin Trans. 1 1974, 1835-1839.
- (1974) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 1835-1839
- Gent, P.A.¹ Gigg, R.²

40
- 77950267156
- This compound is also commercially available.
- This compound is also commercially available.

41
- 23044453589
- J. D. Codée, L. H. Hossain. P. H. Seeberger, Org. Lett. 2005, 7, 3251-3254.
- (2005) Org. Lett. , vol.7 , pp. 3251-3254
- Codée, J.D.¹ Hossain, L.H.² Seeberger, P.H.³

42
- 0001358368
- M. Honda, H. Morita, I. Nagakura, J. Org. Chem. 1997, 62, 8932.
- (1997) J. Org. Chem. , vol.62 , pp. 8932
- Honda, M.¹ Morita, H.² Nagakura, I.³

43
- 0030446219
- W. Dullenkopf, J. C. Castro-Palomino, L. Manzoni, R. R. Schmidt, Carbohydr. Res 1996, 296,135-147.
- (1996) Carbohydr. Res , vol.296 , pp. 135-147
- Dullenkopf, W.¹ Castro-Palomino, J.C.² Manzoni, L.³ Schmidt, R.R.⁴

44
- 84987487370
- W. Bannwarth. A. Trzeciak, Helv. Chim. Acta 1987, 70, 175-186;
- (1987) Helv. Chim. Acta , vol.70 , pp. 175-186
- Bannwarth, W.¹ Trzeciak, A.²

45
- 77950205392
- B. Kratzer, Dissertation, Universität Konstanz, 1994
- B. Kratzer, Dissertation, Universität Konstanz, 1994.

46
- 0027579802
- O. Kanie, S. C. Crawley, M. M. Paleie, O. Hindsgaul, Carbohydr. Res. 1993, 243, 139-164.
- (1993) Carbohydr. Res. , vol.243 , pp. 139-164
- Kanie, O.¹ Crawley, S.C.² Paleie, M.M.³ Hindsgaul, O.⁴

47
- 48349104015
- N. Hada, Y. Shida, H. Shimamura, Y. Sonoda, T. Kasahara, M. Sugita, T Takeda, Carbohydr. Res 2008, 343, 2221-2228.
- (2008) Carbohydr. Res , vol.343 , pp. 2221-2228
- Hada, N.¹ Shida, Y.² Shimamura, H.³ Sonoda, Y.⁴ Kasahara, T.⁵ Sugita, M.⁶ Takeda, T.⁷

48
- 0033842578
- Y-J Hu, R. Dominique. S. K. Das, R. Roy, Can. J. Chem. 2000, 78, 838-845.
- (2000) Can. J. Chem. , vol.78 , pp. 838-845
- Hu, Y.-J.¹ Dominique, R.² Das, S.K.³ Roy, R.⁴

49
- 0001339291
- Wiley
- Fieser & Fieser, Reagents for Organic Synthesis, Vol.1, Wiley, 1967, p. 782.
- (1967) Reagents for Organic Synthesis , vol.1 , pp. 782
- Fieser¹ Fieser²

50
- 0026610897
- T. Behr, W. Fischer, J. Peter-Katalinic, H. Egge, Eur. J. Biochem. 1992, 207, 1063-1075.
- (1992) Eur. J. Biochem. , vol.207 , pp. 1063-1075
- Behr, T.¹ Fischer, W.² Peter-Katalinic, J.³ Egge, H.⁴

51
- 43349087755
- K. Farhat, S. Riekenberg, H. Heine, J. Debarry. R. Lang, J. Mages, U. Buwitt-Beckmann, K. Röschmann, G. Jung, K. H. Wiesmüller, A. J. Ulmer, J. Leukocyte Biol. 2008, 83, 692-701.
- (2008) J. Leukocyte Biol. , vol.83 , pp. 692-701
- Farhat, K.¹ Riekenberg, S.² Heine, H.³ Debarry, J.⁴ Lang, R.⁵ Mages, J.⁶ Buwitt-Beckmann, U.⁷ Röschmann, K.⁸ Jung, G.⁹ Wiesmüller, K.H.¹⁰ Ulmer, A.J.¹¹

52
- 1642506305
- O. Umland, H. Heine, M. Miehe, K. Marienfeld, K. H. Staubach, A. J. Ulmer, J. Leukocyte Biol. 2004, 75, 671-679.
- (2004) J. Leukocyte Biol. , vol.75 , pp. 671-679
- Umland, O.¹ Heine, H.² Miehe, M.³ Marienfeld, K.⁴ Staubach, K.H.⁵ Ulmer, A.J.⁶

53
- 77950255067
- Additional results will be reported in due course.
- Additional results will be reported in due course.

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