SCOPUS 정보 검색 플랫폼

Volumn 69, Issue 48, 2013, Pages 10337-10350

Concise synthesis of di- and trisaccharides related to the O-antigens from Shigella flexneri serotypes 6 and 6a, based on late stage mono-O-acetylation and/or site-selective oxidation

(4) Chassagne, Pierre a,b,c Raibaut, Laurent a,d Guerreiro, Catherine a Mulard, Laurence A a

a INSTITUT PASTEUR (France)

b UNIVERSITÉ PARIS DESCARTES (France)

c TECHNICAL UNIVERSITY OF DENMARK (Denmark)

d UNIV LILLE (France)

Author keywords

Carbohydrates; Glycosylation; Gram negative bacteria; Lipopolysaccharide; TEMPO

Indexed keywords

ACETIC ACID DERIVATIVE; DISACCHARIDE; ETHER DERIVATIVE; GALACTOSE; GALACTURONIC ACID; GLYCOSIDE; O ANTIGEN; OLIGOSACCHARIDE; POLYSACCHARIDE; THIOGLYCOSIDE; TRICHLOROACETIMIDIC ACID; TRISACCHARIDE;

ACETYLATION; ARTICLE; CONTROLLED STUDY; DEPROTECTION REACTION; DIARRHEA; ESCHERICHIA COLI; GLYCOSYLATION; NONHUMAN; OXIDATION; PRIORITY JOURNAL; SENSITIVITY ANALYSIS; SEROTYPE; SHIGELLA FLEXNERI; SYNTHESIS;

ESCHERICHIA COLI; NEGIBACTERIA; SHIGELLA FLEXNERI; SUIDAE;

EID: 84887081257 PISSN: 00404020 EISSN: 14645416 Source Type: Journal
DOI: 10.1016/j.tet.2013.10.011 Document Type: Article

Times cited : (10)

References (49)

1
- 33646127995
- M.M. Levine Vaccine 24 2006 3865 3873
- (2006) Vaccine , vol.24 , pp. 3865-3873
- Levine, M.M.¹

2
- 33749004292
- L. von Seidlein, D.R. Kim, M. Ali, H. Lee, X. Wang, V.D. Thiem, G. Canh do, W. Chaicumpa, M.D. Agtini, A. Hossain, Z.A. Bhutta, C. Mason, O. Sethabutr, K. Talukder, G.B. Nair, J.L. Deen, K. Kotloff, and J. Clemens PLoS Med. 3 2006 1556 1569
- (2006) PLoS Med. , vol.3 , pp. 1556-1569
- Von Seidlein, L.¹ Kim, D.R.² Ali, M.³ Lee, H.⁴ Wang, X.⁵ Thiem, V.D.⁶ Canh Do, G.⁷ Chaicumpa, W.⁸ Agtini, M.D.⁹ Hossain, A.¹⁰ Bhutta, Z.A.¹¹ Mason, C.¹² Sethabutr, O.¹³ Talukder, K.¹⁴ Nair, G.B.¹⁵ Deen, J.L.¹⁶ Kotloff, K.¹⁷ Clemens, J.¹⁸

3
- 0032879806
- K.L. Kotloff, J.P. Winickoff, B. Ivanoff, J.D. Clemens, D.L. Swerdlow, P.J. Sansonetti, G.K. Adak, and M.M. Levine Bull. World Health Organ. 77 1999 651 666
- (1999) Bull. World Health Organ. , vol.77 , pp. 651-666
- Kotloff, K.L.¹ Winickoff, J.P.² Ivanoff, B.³ Clemens, J.D.⁴ Swerdlow, D.L.⁵ Sansonetti, P.J.⁶ Adak, G.K.⁷ Levine, M.M.⁸

4
- 34250353445
- M.M. Levine, K.L. Kotloff, E.M. Barry, M.F. Pasetti, and M.B. Sztein Nat. Rev. Microbiol. 5 2007 540 553
- (2007) Nat. Rev. Microbiol. , vol.5 , pp. 540-553
- Levine, M.M.¹ Kotloff, K.L.² Barry, E.M.³ Pasetti, M.F.⁴ Sztein, M.B.⁵

5
- 42949093134
- M.N. Kweon Curr. Opin. Infect. Dis. 21 2008 313 318
- (2008) Curr. Opin. Infect. Dis. , vol.21 , pp. 313-318
- Kweon, M.N.¹

6
- 77049087280
- J.H. Passwell, S. Ashkenzi, Y. Banet-Levi, R. Ramon-Saraf, N. Farzam, L. Lerner-Geva, H. Even-Nir, B. Yerushalmi, C.Y. Chu, J. Shiloach, J.B. Robbins, R. Schneerson, and I.S.S. Grp Vaccine 28 2010 2231 2235
- (2010) Vaccine , vol.28 , pp. 2231-2235
- Passwell, J.H.¹ Ashkenzi, S.² Banet-Levi, Y.³ Ramon-Saraf, R.⁴ Farzam, N.⁵ Lerner-Geva, L.⁶ Even-Nir, H.⁷ Yerushalmi, B.⁸ Chu, C.Y.⁹ Shiloach, J.¹⁰ Robbins, J.B.¹¹ Schneerson, R.¹² Grp, I.S.S.¹³

7
- 0344959651
- F.R. Noriega, F.M. Liao, D.R. Maneval, S. Ren, S.B. Formal, and M.M. Levine Infect. Immun. 67 1999 782 788
- (1999) Infect. Immun. , vol.67 , pp. 782-788
- Noriega, F.R.¹ Liao, F.M.² Maneval, D.R.³ Ren, S.⁴ Formal, S.B.⁵ Levine, M.M.⁶

8
- 77953872127
- J. Kubler-Kielb, E. Vinogradov, C. Mocca, V. Pozsgay, B. Coxon, J.B. Robbins, and R. Schneerson Carbohydr. Res. 345 2010 1600 1608
- (2010) Carbohydr. Res. , vol.345 , pp. 1600-1608
- Kubler-Kielb, J.¹ Vinogradov, E.² Mocca, C.³ Pozsgay, V.⁴ Coxon, B.⁵ Robbins, J.B.⁶ Schneerson, R.⁷

9
- 61449158708
- A. Phalipon, M. Tanguy, C. Grandjean, C. Guerreiro, F. Belot, D. Cohen, P.J. Sansonetti, and L.A. Mulard J. Immunol. 182 2009 2241 2247
- (2009) J. Immunol. , vol.182 , pp. 2241-2247
- Phalipon, A.¹ Tanguy, M.² Grandjean, C.³ Guerreiro, C.⁴ Belot, F.⁵ Cohen, D.⁶ Sansonetti, P.J.⁷ Mulard, L.A.⁸

10
- 31144470173
- A. Phalipon, C. Costachel, C. Grandjean, A. Thuizat, C. Guerreiro, M. Tanguy, F. Nato, B. Vulliez-Le Normand, F. Belot, K. Wright, V. Marcel-Peyre, P.J. Sansonetti, and L.A. Mulard J. Immunol. 176 2006 1686 1694
- (2006) J. Immunol. , vol.176 , pp. 1686-1694
- Phalipon, A.¹ Costachel, C.² Grandjean, C.³ Thuizat, A.⁴ Guerreiro, C.⁵ Tanguy, M.⁶ Nato, F.⁷ Vulliez-Le Normand, B.⁸ Belot, F.⁹ Wright, K.¹⁰ Marcel-Peyre, V.¹¹ Sansonetti, P.J.¹² Mulard, L.A.¹³

11
- 48249155257
- American Chemical Society Washington DC
- L. Mulard, and A. Phalipon R. Roy, Carbohydrate-based Vaccines Vol. 989 2008 American Chemical Society Washington DC 105 136
- (2008) Carbohydrate-based Vaccines , vol.989 , pp. 105-136
- Mulard, L.¹ Phalipon, A.² Roy, R.³

12
- 84867672999
- A.V. Perepelov, M.E. Shekht, B. Liu, S.D. Shevelev, V.A. Ledov, S.N. Senchenkova, V.L. L'vov, A.S. Shashkov, L. Feng, P.G. Aparin, L. Wang, and Y.A. Knirel FEMS Immunol. Med. Microbiol. 66 2012 201 210
- (2012) FEMS Immunol. Med. Microbiol. , vol.66 , pp. 201-210
- Perepelov, A.V.¹ Shekht, M.E.² Liu, B.³ Shevelev, S.D.⁴ Ledov, V.A.⁵ Senchenkova, S.N.⁶ L'Vov, V.L.⁷ Shashkov, A.S.⁸ Feng, L.⁹ Aparin, P.G.¹⁰ Wang, L.¹¹ Knirel, Y.A.¹²

13
- 0032518320
- K. Hygge Blakeman, A. Weintraub, and G. Widmalm Eur. J. Biochem. 251 1998 534 537
- (1998) Eur. J. Biochem. , vol.251 , pp. 534-537
- Hygge Blakeman, K.¹ Weintraub, A.² Widmalm, G.³

14
- 84879227188
- P. Chassagne, C. Fontana, C. Guerreiro, C. Gauthier, A. Phalipon, G. Widmalm, and L.A. Mulard Eur. J. Org. Chem. 2013 4085 4106
- (2013) Eur. J. Org. Chem. , pp. 4085-4106
- Chassagne, P.¹ Fontana, C.² Guerreiro, C.³ Gauthier, C.⁴ Phalipon, A.⁵ Widmalm, G.⁶ Mulard, L.A.⁷

15
- 64249161490
- J. Boutet, C. Guerreiro, and L.A. Mulard J. Org. Chem. 74 2009 2651 2670
- (2009) J. Org. Chem. , vol.74 , pp. 2651-2670
- Boutet, J.¹ Guerreiro, C.² Mulard, L.A.³

16
- 84867467877
- R. Enugala, L.C.R. Carvalho, M.J.D. Pires, and M.M.B. Marques Chem. - Asian J. 7 2012 2482 2501
- (2012) Chem. - Asian J. , vol.7 , pp. 2482-2501
- Enugala, R.¹ Carvalho, L.C.R.² Pires, M.J.D.³ Marques, M.M.B.⁴

17
- 56049089001
- J. Boutet, and L.A. Mulard Eur. J. Org. Chem. 2008 5526 5542
- (2008) Eur. J. Org. Chem. , pp. 5526-5542
- Boutet, J.¹ Mulard, L.A.²

18
- 84950215313
- R. Gigg, S. Payne, and R. Conant J. Carbohydr. Chem. 2 1983 207 223
- (1983) J. Carbohydr. Chem. , vol.2 , pp. 207-223
- Gigg, R.¹ Payne, S.² Conant, R.³

19
- 0026705545
- M.K. Gurjar, and A.S. Mainkar Tetrahedron 48 1992 6729 6738
- (1992) Tetrahedron , vol.48 , pp. 6729-6738
- Gurjar, M.K.¹ Mainkar, A.S.²

20
- 0034341102
- H. Matsui, J. Furukawa, T. Awano, N. Nishi, and N. Sakairi Chem. Lett. 2000 326 327
- (2000) Chem. Lett. , pp. 326-327
- Matsui, H.¹ Furukawa, J.² Awano, T.³ Nishi, N.⁴ Sakairi, N.⁵

21
- 33749460458
- T. Kajimoto, Y. Ishioka, T. Katoh, and M. Node Bioorg. Med. Chem. Lett. 16 2006 5736 5739
- (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 5736-5739
- Kajimoto, T.¹ Ishioka, Y.² Katoh, T.³ Node, M.⁴

22
- 37649008067
- M. Collot, J. Savreux, and J.M. Mallet Tetrahedron 64 2008 1523 1535
- (2008) Tetrahedron , vol.64 , pp. 1523-1535
- Collot, M.¹ Savreux, J.² Mallet, J.M.³

23
- 0032052505
- J. Bartek, R. Muller, and P. Kosma Carbohydr. Res. 308 1998 259 273
- (1998) Carbohydr. Res. , vol.308 , pp. 259-273
- Bartek, J.¹ Muller, R.² Kosma, P.³

24
- 2542508127
- F. Belot, and J.C. Jacquinet Carbohydr. Res. 325 2000 93 106
- (2000) Carbohydr. Res. , vol.325 , pp. 93-106
- Belot, F.¹ Jacquinet, J.C.²

25
- 0035913760
- D. Crich, and M. Smith J. Am. Chem. Soc. 123 2001 9015 9020
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 9015-9020
- Crich, D.¹ Smith, M.²

26
- 34548132442
- L.J. van den Bos, J.D.C. Codee, R.E.J.N. Litjens, J. Dinkelaar, H.S. Overkleeft, and G.A. van der Marel 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 Marel, G.A.⁶

27
- 0027096896
- C. Vogel, W. Steffan, A.Y. Ott, and V.I. Betaneli Carbohydr. Res. 237 1992 115 129
- (1992) Carbohydr. Res. , vol.237 , pp. 115-129
- Vogel, C.¹ Steffan, W.² Ott, A.Y.³ Betaneli, V.I.⁴

28
- 77949303171
- X.Y. Wu, L.N. Cui, T. Lipinski, and D.R. Bundle Chem. - Eur. J. 16 2010 3476 3488
- (2010) Chem. - Eur. J. , vol.16 , pp. 3476-3488
- Wu, X.Y.¹ Cui, L.N.² Lipinski, T.³ Bundle, D.R.⁴

29
- 0034994242
- M. Haller, and G.J. Boons J. Chem. Soc., Perkin Trans. 1 2001 814 822
- (2001) J. Chem. Soc., Perkin Trans. 1 , pp. 814-822
- Haller, M.¹ Boons, G.J.²

30
- 0033519251
- T. Ren, and D. Liu Bioorg. Med. Chem. Lett. 9 1999 1247 1250
- (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 1247-1250
- Ren, T.¹ Liu, D.²

31
- 0020105861
- B.A. Dmitriev, A.V. Nikolaev, A.S. Shashkov, and N.K. Kochetkov Carbohydr. Res. 100 1982 195 206
- (1982) Carbohydr. Res. , vol.100 , pp. 195-206
- Dmitriev, B.A.¹ Nikolaev, A.V.² Shashkov, A.S.³ Kochetkov, N.K.⁴

32
- 0005915041
- Z. Szurmai, and A. Liptak Carbohydr. Res. 107 1982 33 41
- (1982) Carbohydr. Res. , vol.107 , pp. 33-41
- Szurmai, Z.¹ Liptak, A.²

33
- 0025714056
- Z. Szurmai, A. Liptak, and G. Snatzke Carbohydr. Res. 200 1990 201 208
- (1990) Carbohydr. Res. , vol.200 , pp. 201-208
- Szurmai, Z.¹ Liptak, A.² Snatzke, G.³

34
- 0030991639
- A. Lubineau, K. Basset-Carpentier, and C. Auge Carbohydr. Res. 300 1997 161 167
- (1997) Carbohydr. Res. , vol.300 , pp. 161-167
- Lubineau, A.¹ Basset-Carpentier, K.² Auge, C.³

35
- 52949135897
- J. Boutet, C. Guerreiro, and L.A. Mulard Tetrahedron 64 2008 10558 10572
- (2008) Tetrahedron , vol.64 , pp. 10558-10572
- Boutet, J.¹ Guerreiro, C.² Mulard, L.A.³

36
- 0033515510
- M.Z. Zhao, J. Li, E. Mano, Z.G. Song, D.M. Tschaen, E.J.J. Grabowski, and P.J. Reider J. Org. Chem. 64 1999 2564 2566
- (1999) J. Org. Chem. , vol.64 , pp. 2564-2566
- Zhao, M.Z.¹ Li, J.² Mano, E.³ Song, Z.G.⁴ Tschaen, D.M.⁵ Grabowski, E.J.J.⁶ Reider, P.J.⁷

37
- 0027512468
- N.J. Davis, and S.L. Flitsch Tetrahedron Lett. 34 1993 1181 1184
- (1993) Tetrahedron Lett. , vol.34 , pp. 1181-1184
- Davis, N.J.¹ Flitsch, S.L.²

38
- 33845282179
- P.L. Anelli, C. Biffi, F. Montanari, and S. Quici J. Org. Chem. 52 1987 2559 2562
- (1987) J. Org. Chem. , vol.52 , pp. 2559-2562
- Anelli, P.L.¹ Biffi, C.² Montanari, F.³ Quici, S.⁴

39
- 0029006202
- A.E.J. De Nooy, A.C. Besemer, and H. van Bekkum Tetrahedron 51 1995 8023 8032
- (1995) Tetrahedron , vol.51 , pp. 8023-8032
- De Nooy, A.E.J.¹ Besemer, A.C.² Van Bekkum, H.³

40
- 0036401975
- S. Hanessian, V. Mascitti, P.P. Lu, and H. Ishida Synthesis 2002 1959 1968
- (2002) Synthesis , pp. 1959-1968
- Hanessian, S.¹ Mascitti, V.² Lu, P.P.³ Ishida, H.⁴

41
- 84887100424
- US 6,310,200 B1; (NL), A. N. N. V., Ed.
- Vermaas, D. J. US 6,310,200 B1; (NL), A. N. N. V., Ed., 2001.
- (2001)
- Vermaas, D.J.¹

42
- 0036773819
- J. Xie Eur. J. Org. Chem. 2002 3411 3418
- (2002) Eur. J. Org. Chem. , pp. 3411-3418
- Xie, J.¹

43
- 33745897624
- L.J. Huang, N. Teumelsan, and X.F. Huang Chem. - Eur. J. 12 2006 5246 5252
- (2006) Chem. - Eur. J. , vol.12 , pp. 5246-5252
- Huang, L.J.¹ Teumelsan, N.² Huang, X.F.³

44
- 3142777138
- L.J. van den Bos, J.D.C. Codee, J.C. van der Toorn, T.J. Boltje, J.H. van Boom, H.S. Overkleeft, and G.A. van der Marel Org. Lett. 6 2004 2165 2168
- (2004) Org. Lett. , vol.6 , pp. 2165-2168
- Van Den Bos, L.J.¹ Codee, J.D.C.² Van Der Toorn, J.C.³ Boltje, T.J.⁴ Van Boom, J.H.⁵ Overkleeft, H.S.⁶ Van Der Marel, G.A.⁷

45
- 0035802349
- I. Paterson, G.J. Florence, K. Gerlach, J.P. Scott, and N. Sereinig J. Am. Chem. Soc. 123 2001 9535 9544
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 9535-9544
- Paterson, I.¹ Florence, G.J.² Gerlach, K.³ Scott, J.P.⁴ Sereinig, N.⁵

46
- 6444245214
- M.D. Chappell, C.R. Harris, S.D. Kuduk, A. Balog, Z. Wu, F. Zhang, C.B. Lee, S.J. Stachel, S.J. Danishefsky, T.C. Chou, and Y. Guan J. Org. Chem. 67 2002 7730 7736
- (2002) J. Org. Chem. , vol.67 , pp. 7730-7736
- Chappell, M.D.¹ Harris, C.R.² Kuduk, S.D.³ Balog, A.⁴ Wu, Z.⁵ Zhang, F.⁶ Lee, C.B.⁷ Stachel, S.J.⁸ Danishefsky, S.J.⁹ Chou, T.C.¹⁰ Guan, Y.¹¹

47
- 33745132722
- M. Barbier, T. Breton, K. Servat, E. Grand, B. Kokoh, and J. Kovensky J. Carbohydr. Chem. 25 2006 253 266
- (2006) J. Carbohydr. Chem. , vol.25 , pp. 253-266
- Barbier, M.¹ Breton, T.² Servat, K.³ Grand, E.⁴ Kokoh, B.⁵ Kovensky, J.⁶

48
- 84880023232
- K. Ohara, C.C. Lin, P.J. Yang, W.T. Hung, W.B. Yang, T.J.R. Cheng, J.M. Fang, and C.H. Wong J. Org. Chem. 78 2013 6390 6411
- (2013) J. Org. Chem. , vol.78 , pp. 6390-6411
- Ohara, K.¹ Lin, C.C.² Yang, P.J.³ Hung, W.T.⁴ Yang, W.B.⁵ Cheng, T.J.R.⁶ Fang, J.M.⁷ Wong, C.H.⁸

49
- 46949083185
- M.U. Roslund, O. Aitio, J. Warna, H. Maaheimo, D.Y. Murzin, and R. Leino J. Am. Chem. Soc. 130 2008 8769 8772
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 8769-8772
- Roslund, M.U.¹ Aitio, O.² Warna, J.³ Maaheimo, H.⁴ Murzin, D.Y.⁵ Leino, R.⁶

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.