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Carbohydrate Research

Volumn 345, Issue 16, 2010, Pages 2328-2333

Synthesis of seleno-carbohydrates derived from d-galactose

(4) Braga, Hugo C a Wouters, Ana D a Zerillo, Felipe B a Lüdtke, Diogo S a

a UNIVERSITY OF SÃO PAULO (Brazil)

Author keywords

Carbohydrates; Galactopyranosides; Selenium; Seleno carbohydrates

Indexed keywords

ALKYL SUBSTITUENT; D-GALACTOSE; GALACTOPYRANOSIDES; PROPARGYL; SELENO-CARBOHYDRATES; STRUCTURAL VARIATIONS;

COMPLEXATION; LIBRARIES; SELENIUM; SELENIUM COMPOUNDS;

CARBOHYDRATES;

CARBOHYDRATE; ELECTROPHILE; GALACTOSE; PYRANOSIDE; SELENIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; MICHAEL ADDITION; NUCLEOPHILICITY; PRIORITY JOURNAL; SYNTHESIS;

CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; GALACTOSE; ORGANOSELENIUM COMPOUNDS; SELENIUM; STEREOISOMERISM;

EID: 77958089492 PISSN: 00086215 EISSN: None Source Type: Journal
DOI: 10.1016/j.carres.2010.08.019 Document Type: Article

Times cited : (31)

References (56)

1
- 0025953866
- T.C. Stadtman J. Biol. Chem. 266 1991 16257 16260
- (1991) J. Biol. Chem. , vol.266 , pp. 16257-16260
- Stadtman, T.C.¹

2
- 0030008330
- T.C. Stadtman Annu. Rev. Biochem. 65 1996 83 100
- (1996) Annu. Rev. Biochem. , vol.65 , pp. 83-100
- Stadtman, T.C.¹

3
- 0035997346
- T.C. Stadtman Annu. Rev. Biochem. 71 2002 1 16
- (2002) Annu. Rev. Biochem. , vol.71 , pp. 1-16
- Stadtman, T.C.¹

4
- 12844265308
- Y. Ogasawara, G.M. Lacourciere, K. Ishii, and T.C. Stadtman Proc. Natl. Acad. Sci. U.S.A. 102 2005 1012 1016
- (2005) Proc. Natl. Acad. Sci. U.S.A. , vol.102 , pp. 1012-1016
- Ogasawara, Y.¹ Lacourciere, G.M.² Ishii, K.³ Stadtman, T.C.⁴

5
- 0038442808
- G.V. Kryukov, S. Castello, S.V. Novoselov, A.V. Lobanov, O. Zehtab, R. Guigó, and V.N. Gladyshev Science 300 2003 1439 1443
- (2003) Science , vol.300 , pp. 1439-1443
- Kryukov, G.V.¹ Castello, S.² Novoselov, S.V.³ Lobanov, A.V.⁴ Zehtab, O.⁵ Guigó, R.⁶ Gladyshev, V.N.⁷

6
- 35348902569
- For an excellent review on the comparison of selenium and sulfur in chemistry and biochemistry, see: L.A. Wessjohann, A. Schneider, M. Abbas, and W. Brandt Biol. Chem. 388 2007 997 1006
- (2007) Biol. Chem. , vol.388 , pp. 997-1006
- Wessjohann, L.A.¹ Schneider, A.² Abbas, M.³ Brandt, W.⁴

7
- 1642625262
- L.C. Clark, G.F. Combs, B.W. Turnbull, E.H. Slate, D.K. Chalker, J. Chow, L.S. Davis, R.A. Glover, G.F. Graham, E.G. Gross, A. Krongrad, J.L. Lesher, H.K. Park, B.B. Sanders, C.L. Smith, and J.R. Taylor J. Am. Med. Assoc. 276 1996 1957 1963
- (1996) J. Am. Med. Assoc. , vol.276 , pp. 1957-1963
- Clark, L.C.¹ Combs, G.F.² Turnbull, B.W.³ Slate, E.H.⁴ Chalker, D.K.⁵ Chow, J.⁶ Davis, L.S.⁷ Glover, R.A.⁸ Graham, G.F.⁹ Gross, E.G.¹⁰ Krongrad, A.¹¹ Lesher, J.L.¹² Park, H.K.¹³ Sanders, B.B.¹⁴ Smith, C.L.¹⁵ Taylor, J.R.¹⁶

8
- 70350491939
- O. Micke, L. Schomburg, J. Buentzer, K. Kisters, and R. Muecke Molecules 14 2009 3975 3988
- (2009) Molecules , vol.14 , pp. 3975-3988
- Micke, O.¹ Schomburg, L.² Buentzer, J.³ Kisters, K.⁴ Muecke, R.⁵

9
- 0034662094
- M.P. Rayman Lancet 356 2000 233 241
- (2000) Lancet , vol.356 , pp. 233-241
- Rayman, M.P.¹

10
- 0035839432
- F.J. Martin-Romero, G.V. Kryukov, A.V. Lobanov, B.A. Carlson, B.J. Lee, V.N. Gladyshev, and D.L. Hatfield J. Biol. Chem. 276 2001 29798 29804
- (2001) J. Biol. Chem. , vol.276 , pp. 29798-29804
- Martin-Romero, F.J.¹ Kryukov, G.V.² Lobanov, A.V.³ Carlson, B.A.⁴ Lee, B.J.⁵ Gladyshev, V.N.⁶ Hatfield, D.L.⁷

11
- 0033610030
- F. Ursini, S. Heim, M. Kiess, M. Maiorino, A. Roveri, J. Wissing, and L. Flohe Science 285 1999 1393 1396
- (1999) Science , vol.285 , pp. 1393-1396
- Ursini, F.¹ Heim, S.² Kiess, M.³ Maiorino, M.⁴ Roveri, A.⁵ Wissing, J.⁶ Flohe, L.⁷

12
- 0003629457
- Wiley-Interscience New York
- D.L. Klayman, and W.H.H. Günter Organoselenium Compounds: Their Chemistry and Biology 1973 Wiley-Interscience New York
- (1973) Organoselenium Compounds: Their Chemistry and Biology
- Klayman, D.L.¹ Günter, W.H.H.²

13
- 0003466340
- Plenum Press New York
- R.J. Shamberger Biochemistry of Selenium 1983 Plenum Press New York
- (1983) Biochemistry of Selenium
- Shamberger, R.J.¹

14
- 0035385139
- G. Mugesh, W.-W. du Mont, and H. Sies Chem. Rev. 101 2001 2125 2179
- (2001) Chem. Rev. , vol.101 , pp. 2125-2179
- Mugesh, G.¹ Du Mont, W.-W.² Sies, H.³

15
- 84984583119
- C.W. Nogueira, G. Zeni, and J.B.T. Rocha Chem. Rev. 104 2004 6255 6285
- (2004) Chem. Rev. , vol.104 , pp. 6255-6285
- Nogueira, C.W.¹ Zeni, G.² Rocha, J.B.T.³

16
- 46249134106
- B.K. Sarma, and G. Mugesh Org. Biomol. Chem. 6 2008 965 974
- (2008) Org. Biomol. Chem. , vol.6 , pp. 965-974
- Sarma, B.K.¹ Mugesh, G.²

17
- 45549086618
- L.A. Wessjohann, and A. Schneider Chem. Biodiv. 5 2008 375 388
- (2008) Chem. Biodiv. , vol.5 , pp. 375-388
- Wessjohann, L.A.¹ Schneider, A.²

18
- 47749147368
- M. Abdo, and S. Knapp J. Am. Chem. Soc. 130 2008 9234 9235
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 9234-9235
- Abdo, M.¹ Knapp, S.²

19
- 53549096011
- M. Abdo, S. Liu, B. Zhou, C.D. Walls, L. Wu, S. Knapp, and Z.Y. Zhang J. Am. Chem. Soc. 130 2008 13196 13197
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 13196-13197
- Abdo, M.¹ Liu, S.² Zhou, B.³ Walls, C.D.⁴ Wu, L.⁵ Knapp, S.⁶ Zhang, Z.Y.⁷

20
- 34547933514
- H. Liu, R. Nasi, K. Jayakanthan, L. Sim, H. Heipel, D.R. Rose, and B.M. Pinto J. Org. Chem. 72 2007 6562 6572
- (2007) J. Org. Chem. , vol.72 , pp. 6562-6572
- Liu, H.¹ Nasi, R.² Jayakanthan, K.³ Sim, L.⁴ Heipel, H.⁵ Rose, D.R.⁶ Pinto, B.M.⁷

21
- 12344279774
- H. Liu, and B.M. Pinto J. Org. Chem. 70 2005 753 755
- (2005) J. Org. Chem. , vol.70 , pp. 753-755
- Liu, H.¹ Pinto, B.M.²

22
- 0008151422
- K. Blumberg, A. Fuccello, and T. Van Es Carbohydr. Res. 59 1977 351 362
- (1977) Carbohydr. Res. , vol.59 , pp. 351-362
- Blumberg, K.¹ Fuccello, A.² Van Es, T.³

23
- 33645221441
- S.J. Ahn, M. Koketsu, H. Ishihara, S.M. Lee, S.K. Ha, K.H. Lee, T.H. Kang, and S.Y. Kim Chem. Pharm. Bull. 54 2006 281 286
- (2006) Chem. Pharm. Bull. , vol.54 , pp. 281-286
- Ahn, S.J.¹ Koketsu, M.² Ishihara, H.³ Lee, S.M.⁴ Ha, S.K.⁵ Lee, K.H.⁶ Kang, T.H.⁷ Kim, S.Y.⁸

24
- 0037059010
- Y. Kobayashi, Y. Ogra, K. Ishiwata, H. Takayama, N. Aimi, and T. Suzuki Proc. Natl. Acad. Sci. U.S.A. 99 2002 15932 15936
- (2002) Proc. Natl. Acad. Sci. U.S.A. , vol.99 , pp. 15932-15936
- Kobayashi, Y.¹ Ogra, Y.² Ishiwata, K.³ Takayama, H.⁴ Aimi, N.⁵ Suzuki, T.⁶

25
- 0026338152
- N.M. Goudgaeon, and R.F. Schinazi J. Med. Chem. 34 1991 3305 3309
- (1991) J. Med. Chem. , vol.34 , pp. 3305-3309
- Goudgaeon, N.M.¹ Schinazi, R.F.²

26
- 0034687232
- C.K. Chu, L. Ma, S. Olgen, C. Pierra, J. Du, G. Gumina, E. Gullen, Y.-C. Cheng, and R.F. Schinazi J. Med. Chem. 43 2000 3906 3912
- (2000) J. Med. Chem. , vol.43 , pp. 3906-3912
- Chu, C.K.¹ Ma, L.² Olgen, S.³ Pierra, C.⁴ Du, J.⁵ Gumina, G.⁶ Gullen, E.⁷ Cheng, Y.-C.⁸ Schinazi, R.F.⁹

27
- 77950814017
- A.E.A. Hassan, J. Sheng, W. Zhang, and Z. Huang J. Am. Chem. Soc. 132 2010 2120 2121
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 2120-2121
- Hassan, A.E.A.¹ Sheng, J.² Zhang, W.³ Huang, Z.⁴

28
- 19244379910
- C. Höbartner, and R. Micura J. Am. Chem. Soc. 126 2004 1141 1149
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 1141-1149
- Höbartner, C.¹ Micura, R.²

29
- 2342468599
- Y. Buzin, N. Carrasco, and Z. Huang Org. Lett. 6 2004 1099 1102
- (2004) Org. Lett. , vol.6 , pp. 1099-1102
- Buzin, Y.¹ Carrasco, N.² Huang, Z.³

30
- 29444435858
- J. Salon, G. Chen, Y. Portilla, M.W. Germann, and Z. Huang Org. Lett. 7 2005 5645 5648
- (2005) Org. Lett. , vol.7 , pp. 5645-5648
- Salon, J.¹ Chen, G.² Portilla, Y.³ Germann, M.W.⁴ Huang, Z.⁵

31
- 77951173411
- For a recent review, see: J. Sheng, and Z. Huang Chem. Biodiv. 7 2010 753 785
- (2010) Chem. Biodiv. , vol.7 , pp. 753-785
- Sheng, J.¹ Huang, Z.²

32
- 0035969598
- S. Yamago, T. Yamada, O. Hara, H. Ito, Y. Mino, and J.-I. Yoshida Org. Lett. 3 2001 3867 3870
- (2001) Org. Lett. , vol.3 , pp. 3867-3870
- Yamago, S.¹ Yamada, T.² Hara, O.³ Ito, H.⁴ Mino, Y.⁵ Yoshida, J.-I.⁶

33
- 33751386390
- S. Mehta, and B.M. Pinto J. Org. Chem. 58 1993 3269 3276
- (1993) J. Org. Chem. , vol.58 , pp. 3269-3276
- Mehta, S.¹ Pinto, B.M.²

34
- 0031448014
- B.D. Johnston, and B.M. Pinto Carbohydr. Res. 305 1998 289 292
- (1998) Carbohydr. Res. , vol.305 , pp. 289-292
- Johnston, B.D.¹ Pinto, B.M.²

35
- 4444332884
- D.J. Chambers, G.R. Evans, and A.J. Fairbanks Tetrahedron 60 2004 8411 8419
- (2004) Tetrahedron , vol.60 , pp. 8411-8419
- Chambers, D.J.¹ Evans, G.R.² Fairbanks, A.J.³

36
- 0442264159
- L. Grant, Y. Liu, K.E. Walsh, D.S. Walter, and T. Gallagher Org. Lett. 4 2002 4623 4625
- (2002) Org. Lett. , vol.4 , pp. 4623-4625
- Grant, L.¹ Liu, Y.² Walsh, K.E.³ Walter, D.S.⁴ Gallagher, T.⁵

37
- 0034701517
- W.-T. Jiaang, M.-Y. Chang, P.-H. Tseng, and S.-T. Chen Tetrahedron Lett. 41 2000 3127 3130
- (2000) Tetrahedron Lett. , vol.41 , pp. 3127-3130
- Jiaang, W.-T.¹ Chang, M.-Y.² Tseng, P.-H.³ Chen, S.-T.⁴

38
- 77950594227
- H.C. Braga, H.A. Stefani, M.W. Paixão, F.W. Santos, and D.S. Lüdtke Tetrahedron 66 2010 3441 3446
- (2010) Tetrahedron , vol.66 , pp. 3441-3446
- Braga, H.C.¹ Stefani, H.A.² Paixão, M.W.³ Santos, F.W.⁴ Lüdtke, D.S.⁵

39
- 58149195370
- A.S. Vieira, P.F. Fiorante, T.L.S. Hough, F.P. Ferreira, D.S. Lüdtke, and H.A. Stefani Org. Lett. 10 2008 5215 5218
- (2008) Org. Lett. , vol.10 , pp. 5215-5218
- Vieira, A.S.¹ Fiorante, P.F.² Hough, T.L.S.³ Ferreira, F.P.⁴ Lüdtke, D.S.⁵ Stefani, H.A.⁶

40
- 65449163366
- A.L. Braga, W.A. Severo-Filho, R.S. Schwab, O.E.D. Rodrigues, L. Dornelles, H.C. Braga, and D.S. Lüdtke Tetrahedron Lett. 50 2009 3005 3007
- (2009) Tetrahedron Lett. , vol.50 , pp. 3005-3007
- Braga, A.L.¹ Severo-Filho, W.A.² Schwab, R.S.³ Rodrigues, O.E.D.⁴ Dornelles, L.⁵ Braga, H.C.⁶ Lüdtke, D.S.⁷

41
- 77950845385
- A.D. Wouters, G.H.G. Trossini, H.A. Stefani, and D.S. Lüdtke Eur. J. Org. Chem. 2010 2351 2356
- (2010) Eur. J. Org. Chem. , pp. 2351-2356
- Wouters, A.D.¹ Trossini, G.H.G.² Stefani, H.A.³ Lüdtke, D.S.⁴

42
- 68249105306
- For an interesting overview on the opportunities in the chemistry of carbohydrates, see: V.F. Ferreira, D.R. Rocha, and F.D. Silva Quim. Nova 32 2009 623 638
- (2009) Quim. Nova , vol.32 , pp. 623-638
- Ferreira, V.F.¹ Rocha, D.R.² Silva, F.D.³

43
- 0001378449
- K.P.R. Kartha Tetrahedron Lett. 27 1986 3415 3416
- (1986) Tetrahedron Lett. , vol.27 , pp. 3415-3416
- Kartha, K.P.R.¹

44
- 49349140545
- D. Liotta, W. Markiewickz, and H. Santiesteban Tetrahedron Lett. 16 1977 4365 4368
- (1977) Tetrahedron Lett. , vol.16 , pp. 4365-4368
- Liotta, D.¹ Markiewickz, W.² Santiesteban, H.³

45
- 32444450704
- A.L. Braga, D.S. Lüdtke, and E.E. Alberto J. Braz. Chem. Soc. 17 2006 11 15
- (2006) J. Braz. Chem. Soc. , vol.17 , pp. 11-15
- Braga, A.L.¹ Lüdtke, D.S.² Alberto, E.E.³

46
- 0141631574
- A.L. Braga, M.W. Paixão, D.S. Lüdtke, C.C. Silveira, and O.E.D. Rodrigues Org. Lett. 5 2003 2635 2638
- (2003) Org. Lett. , vol.5 , pp. 2635-2638
- Braga, A.L.¹ Paixão, M.W.² Lüdtke, D.S.³ Silveira, C.C.⁴ Rodrigues, O.E.D.⁵

47
- 0000038588
- J.A. Gladysz, J.L. Hornby, and J.E. Garbe J. Org. Chem. 43 1978 1204 1208
- (1978) J. Org. Chem. , vol.43 , pp. 1204-1208
- Gladysz, J.A.¹ Hornby, J.L.² Garbe, J.E.³

48
- 77949643536
- D.S. Rampon, F.S. Rodembusch, J.M.F.M. Schneider, I.H. Bechtold, P.F.B. Goncalves, A.A. Merlo, and P.H. Schneider J. Mater. Chem. 20 2010 715 722
- (2010) J. Mater. Chem. , vol.20 , pp. 715-722
- Rampon, D.S.¹ Rodembusch, F.S.² Schneider, J.M.F.M.³ Bechtold, I.H.⁴ Goncalves, P.F.B.⁵ Merlo, A.A.⁶ Schneider, P.H.⁷

49
- 62749160806
- A.F. Keppler, R.A. Gariani, D.G. Lopes, and J.V. Comasseto Tetrahedron Lett. 50 2009 2181 2184
- (2009) Tetrahedron Lett. , vol.50 , pp. 2181-2184
- Keppler, A.F.¹ Gariani, R.A.² Lopes, D.G.³ Comasseto, J.V.⁴

50
- 0037170130
- F.K. Zinn, V.E. Righi, S.C. Luque, H.B. Formiga, and J.V. Comasseto Tetrahedron Lett. 43 2002 1625 1628
- (2002) Tetrahedron Lett. , vol.43 , pp. 1625-1628
- Zinn, F.K.¹ Righi, V.E.² Luque, S.C.³ Formiga, H.B.⁴ Comasseto, J.V.⁵

51
- 27644451000
- 4 in EtOH: A.L. Braga, D.S. Lüdtke, J.A. Sehnem, and E.E. Alberto Tetrahedron 61 2005 11664 11671
- (2005) Tetrahedron , vol.61 , pp. 11664-11671
- Braga, A.L.¹ Lüdtke, D.S.² Sehnem, J.A.³ Alberto, E.E.⁴

52
- 33947727055
- R. Chinchilla, and C. Najera Chem. Rev. 107 2007 874 922
- (2007) Chem. Rev. , vol.107 , pp. 874-922
- Chinchilla, R.¹ Najera, C.²

53
- 84879868832
- M. Oestreich, John Wiley & Sons Chichester, UK
- M. Oestreich, The Mizoroki-Heck Reaction 2009 John Wiley & Sons Chichester, UK
- (2009) The Mizoroki-Heck Reaction

54
- 0000096835
- H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004 2021
- (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2004-2021
- Kolb, H.C.¹ Finn, M.G.² Sharpless, K.B.³

55
- 0002714675
- W.C. Still, M. Kahn, and A. Mitra J. Org. Chem. 43 1978 2923 2925
- (1978) J. Org. Chem. , vol.43 , pp. 2923-2925
- Still, W.C.¹ Kahn, M.² Mitra, A.³

56
- 0035946004
- Y. Lu, and G. Just Tetrahedron 57 2001 1677 1687
- (2001) Tetrahedron , vol.57 , pp. 1677-1687
- Lu, Y.¹ Just, G.²

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