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Angewandte Chemie - International Edition

Volumn 49, Issue 3, 2010, Pages 602-606

Highly enantioselective recognition of structurally diverse α-Hydroxycarboxylic acids using a fluorescent sensor

(7) Liu, Hai Lin a Peng, Qian a Wu, Yun Dong a,c Chen, Di a Hou, Xue Long a Sabat, Michal b Pu, Lin b

a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY (China)

b UNIVERSITY OF VIRGINIA (United States)

c HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY (Hong Kong)

Author keywords

hydroxycarboxylic acids; Amino alcohols; Enantioselectivity; Fluorescence; Sensors

Indexed keywords

AMINO ALCOHOLS; ENANTIOSELECTIVE; ENANTIOSELECTIVE RECOGNITION; FLUORESCENCE SENSORS; FLUORESCENT SENSORS;

ALCOHOLS; AMINES; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; FLUORESCENCE; SENSORS;

ACIDS;

CARBOXYLIC ACID; FLUORESCENT DYE; HYDROXYACID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

CARBOXYLIC ACIDS; FLUORESCENT DYES; HYDROXY ACIDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 74549124419 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.200904889 Document Type: Article

Times cited : (113)

References (70)

1
- 0000425928
- For reviews, see: a) M. T. Reetz, Angew. Chem. 2002, 114, 1391- 1394;
- (2002) Angew. Chem. , vol.114 , pp. 1391-1394
- Reetz, M.T.¹

2
- 0037090667
- Angew. Chem. Int. Ed. 2002, 41, 1335-1338;
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1335-1338

3
- 0001564142
- b)M. Tsukamoto, H. B. Kagan, Adv. Synth. Catal. 2002, 344, 453-463;
- (2002) Adv. Synth. Catal. , vol.344 , pp. 453-463
- Tsukamoto, M.¹ Kagan, H.B.²

4
- 0036084211
- c) M. G. Finn, Chirality 2002, 14, 534-540;
- (2002) Chirality , vol.14 , pp. 534-540
- Finn, M.G.¹

5
- 0031732777
- d) K. D. Shimizu, M. L. Snapper, A. H. Hoveyda, Chem. Eur. J. 1998, 4, 1885-1889.
- (1998) Chem. Eur. J. , vol.4 , pp. 1885-1889
- Shimizu, K.D.¹ Snapper, M.L.² Hoveyda, A.H.³

6
- 0000999637
- For selected examples
- For selected examples, see: a) J. Guo, J. Wu, G. Siuzdak, M. G. Finn, Angew. Chem. 1999, 111, 1868-1871;
- (1999) Angew. Chem. , vol.111 , pp. 1868-1871
- Guo, J.¹ Wu, J.² Siuzdak, G.³ Finn, M.G.⁴

7
- 0033553799
- Angew. Chem. Int. Ed. 1999, 38, 1755-1758;
- (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1755-1758

8
- 0001753183
- b) M. T. Reetz, M. H. Becker, H. W. Klein,D. Stöckigt, Angew. Chem. 1999, 111, 1872-1875;
- (1999) Angew. Chem. , vol.111 , pp. 1872-1875
- Reetz, M.T.¹ Becker, M.H.² Klein, H.W.³ Stöckigt, D.⁴

9
- 0033553835
- Angew. Chem. Int. Ed. 1999, 38, 1758-1761;
- (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1758-1761

10
- 0000627893
- c) M.T. Reetz, M. H. Becker, K. M. Kühling, A. Holzwarth, Angew. Chem. 1998, 110, 2792-2795;
- (1998) Angew. Chem. , vol.110 , pp. 2792-2795
- Reetz, M.T.¹ Becker, M.H.² Kühling, K.M.³ Holzwarth, A.⁴

11
- 0032538361
- Angew. Chem. Int. Ed. 1998, 37, 2647-2650;
- (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 2647-2650

12
- 0000545849
- d) M.T. Reetz, K.M. Kühling, A. Deege, H. Hinrichs, D. Belder, Angew. Chem. 2000, 112, 4049-4052;
- (2000) Angew. Chem. , vol.112 , pp. 4049-4052
- Reetz, M.T.¹ Kühling, K.M.² Deege, A.³ Hinrichs, H.⁴ Belder, D.⁵

13
- 0034602059
- Angew. Chem. Int. Ed 2000, 39, 3891-3893;
- (2000) Angew. Chem. Int. Ed , vol.39 , pp. 3891-3893

14
- 0001704546
- e) K. Ding, A. Ishii, K. Mikami, Angew. Chem. 1999, 111, 519-523;
- (1999) Angew. Chem. , vol.111 , pp. 519-523
- Ding, K.¹ Ishii, A.² Mikami, K.³

15
- 0033557464
- Angew. Chem. Int. Ed. 1999, 38, 497-501;
- (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 497-501

16
- 0035913739
- f) P. Abato, C. T. Seto, J. Am. Chem. Soc. 2001, 123, 9206-9207.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 9206-9207
- Abato, P.¹ Seto, C.T.²

17
- 1842430722
- a For a Review on enantioselective fluorescent sensing
- a) For a Review on enantioselective fluorescent sensing, see: L. Pu, Chem. Rev. 2004, 104, 1687-1716.
- (2004) Chem. Rev. , vol.104 , pp. 1687-1716
- Pu, L.¹

18
- 34547710746
- Selected Reviews on using fluorescence in sensing: b RSC, UK
- Selected Reviews on using fluorescence in sensing: b) T. D. James, M. D. Phillips, S. Shinkai, Boronic Acids in Saccharide Recognition, RSC, UK, 2006;
- (2006) Boronic Acids in Saccharide Recognition
- James, T.D.¹ Phillips, M.D.² Shinkai, S.³

19
- 40449141631
- c) C. McDonagh, C. S. Burke, B. D. MacCraith, Chem. Rev. 2008, 108, 400-422;
- (2008) Chem. Rev. , vol.108 , pp. 400-422
- McDonagh, C.¹ Burke, C.S.² MacCraith, B.D.³

20
- 40449109993
- d) S. M. Borisov, O. S. Wolfbeis, Chem. Rev. 2008, 108, 423-461;
- (2008) Chem. Rev. , vol.108 , pp. 423-461
- Borisov, S.M.¹ Wolfbeis, O.S.²

21
- 33847753435
- e) K. S. Johnson, J. A. Needoba, S. C. Riser, W. J. Showers, Chem. Rev. 2007, 107, 623-640;
- (2007) Chem. Rev. , vol.107 , pp. 623-640
- Johnson, K.S.¹ Needoba, J.A.² Riser, S.C.³ Showers, W.J.⁴

22
- 11144268184
- f) R. Jelinek, S. Kolusheva, Chem. Rev. 2004, 104, 5987-6015;
- (2004) Chem. Rev. , vol.104 , pp. 5987-6015
- Jelinek, R.¹ Kolusheva, S.²

23
- 61849151435
- g) E. M. Nolan, S. J. Lippard, Acc. Chem. Res. 2009, 42, 193-203;
- (2009) Acc. Chem. Res. , vol.42 , pp. 193-203
- Nolan, E.M.¹ Lippard, S.J.²

24
- 33845304562
- CRC, U.S.
- h) R. B. Thompson, Fluorescence Sensors and Biosensors, CRC, U.S., 2005;
- (2005) Fluorescence Sensors and Biosensors
- Thompson, R.B.¹

25
- 74549117837
- (Ed.: A. W. Czarnik), American Chemical Society, Washington, DC, ACS Symposium Series 538
- i) Fluorescent Chemosensors for Ion and Molecular Recognition (Ed.: A. W. Czarnik), American Chemical Society, Washington, DC, 1993 (ACS Symposium Series 538);
- (1993) Fluorescent Chemosensors for Ion and Molecular Recognition

26
- 0031191655
- j) A. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher, T. E. Rice, Chem. Rev. 1997, 97, 1515-1566;
- (1997) Chem. Rev. , vol.97 , pp. 1515-1566
- De Silva, A.P.¹ Gunaratne, H.Q.N.² Gunnlaugsson, T.³ Huxley, A.J.M.⁴ McCoy, C.P.⁵ Rademacher, J.T.⁶ Rice, T.E.⁷

27
- 11944268448
- k) L. Fabbrizzi, A. Poggi, Chem. Soc. Rev. 1995, 24, 197-202;
- (1995) Chem. Soc. Rev. , vol.24 , pp. 197-202
- Fabbrizzi, L.¹ Poggi, A.²

28
- 0003608524
- 2nd ed. (Ed.: W T. Mason), Academic, San Diego
- Fluorescent and Luminescent Probes, 2nd ed. (Ed.: W T. Mason), Academic, San Diego, 1999;
- (1999) Fluorescent and Luminescent Probes

29
- 34249732618
- m) L. BasabeDesmonts, D. N. Reinhoudt, M. Crego-Calama, Chem. Soc. Rev. 2007, 36, 993-1017.
- (2007) Chem. Soc. Rev. , vol.36 , pp. 993-1017
- Basabedesmonts, L.¹ Reinhoudt, D.N.² Crego-Calama, M.³

30
- 0001679632
- For examples using fluorescence in chiral analysis
- For examples using fluorescence in chiral analysis, see: a) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Angew. Chem. 1996, 108, 2038-2050;
- (1996) Angew. Chem. , vol.108 , pp. 2038-2050
- James, T.D.¹ Sandanayake, K.R.A.S.² Shinkai, S.³

31
- 0029902912
- Angew. Chem. Int. Ed. Engl. 1996, 35, 1910-1922;
- (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 1910-1922

32
- 0029272840
- b) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Nature 1995, 374, 345-347;
- (1995) Nature , vol.374 , pp. 345-347
- James, T.D.¹ Sandanayake, K.R.A.S.² Shinkai, S.³

33
- 1842575507
- c) A. P. de Silva, Nature 1995, 374, 310;
- (1995) Nature , vol.374 , pp. 310
- De Silva, A.P.¹

34
- 0030944785
- d) M. Takeuchi, S. Yoda, T. Imada, S. Shinkai, Tetrahedron 1997, 53, 8335-8348;
- (1997) Tetrahedron , vol.53 , pp. 8335-8348
- Takeuchi, M.¹ Yoda, S.² Imada, T.³ Shinkai, S.⁴

35
- 17044398230
- e) J. Z. Zhao, T. M. Fyles, T. D. James, Angew. Chem. 2004, 116, 3543-3546;
- (2004) Angew. Chem. , vol.116 , pp. 3543-3546
- Zhao, J.Z.¹ Fyles, T.M.² James, T.D.³

36
- 4544246864
- Angew. Chem. Int. Ed. 2004, 43, 3461-3464;
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 3461-3464

37
- 64549104886
- f) F. Han, L. N. Chi, X. F. Liang, S. M. Ji, S. S. Liu, F. K. Zhou, Y. B. Wu, K. L. Han, J. Z. Zhao, T. D. James, J. Org. Chem. 2009, 74, 1333-1336;
- (2009) J. Org. Chem. , vol.74 , pp. 1333-1336
- Han, F.¹ Chi, L.N.² Liang, X.F.³ Ji, S.M.⁴ Liu, S.S.⁵ Zhou, F.K.⁶ Wu, Y.B.⁷ Han, K.L.⁸ Zhao, J.Z.⁹ James, T.D.¹⁰

38
- 0000876784
- g) V. Pugh, Q. S. Hu, L. Pu, Angew. Chem. 2000, 112, 3784-3787;
- (2000) Angew. Chem. , vol.112 , pp. 3784-3787
- Pugh, V.¹ Hu, Q.S.² Pu, L.³

39
- 0034675568
- Angew. Chem. Int. Ed. 2000, 39, 3638-3641;
- (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3638-3641

40
- 0035953064
- h) M. T. Reetz, S. Sostmann, Tetrahedron 2001, 57, 2515-2520;
- (2001) Tetrahedron , vol.57 , pp. 2515-2520
- Reetz, M.T.¹ Sostmann, S.²

41
- 0035900973
- i) G. A. Korbel, G. Lalic, M. D. Shair, J. Am. Chem. Soc. 2001, 123, 361-362;
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 361-362
- Korbel, G.A.¹ Lalic, G.² Shair, M.D.³

42
- 0035838880
- j) E. R. Jarvo, C. A. Evans, G. T. Copeland, S. J. Miller, J. Org. Chem. 2001, 66, 5522-5527;
- (2001) J. Org. Chem. , vol.66 , pp. 5522-5527
- Jarvo, E.R.¹ Evans, C.A.² Copeland, G.T.³ Miller, S.J.⁴

43
- 1442325392
- k) W. L. Wong, K. H. Huang, P. F. Teng, C. S. Lee, H. L. Kwong, Chem. Commun. 2004, 384-385;
- (2004) Chem. Commun. , pp. 384-385
- Wong, W.L.¹ Huang, K.H.² Teng, P.F.³ Lee, C.S.⁴ Kwong, H.L.⁵

44
- 3042616833
- S. Pagliari, R. Corradini, G. Galaverna, S. Sforza, A. Dossena, M. Montalti, L. Prodi, N. Zaccheroni, R. Marchelli, Chem. Eur. J. 2004, 10, 2749-2758;
- (2004) Chem. Eur. J. , vol.10 , pp. 2749-2758
- Pagliari, S.¹ Corradini, R.² Galaverna, G.³ Sforza, S.⁴ Dossena, A.⁵ Montalti, M.⁶ Prodi, L.⁷ Zaccheroni, N.⁸ Marchelli, R.⁹

45
- 74549172955
- m) G. Klein, J. L. Reymond, Helv. Chim. Acta 1999, 82, 400407.
- (1999) Helv. Chim. Acta , vol.82 , pp. 400407
- Klein, G.¹ Reymond, J.L.²

46
- 1642404953
- a) L. Zhu, E. V. Anslyn, J. Am. Chem. Soc. 2004, 126, 3676-3677;
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 3676-3677
- Zhu, L.¹ Anslyn, E.V.²

47
- 16244420077
- b) L. Zhu, Z. Zhong, E. V. Anslyn, J. Am. Chem. Soc. 2005, 127, 4260-4269.
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 4260-4269
- Zhu, L.¹ Zhong, Z.² Anslyn, E.V.³

48
- 0001509181
- a) F. Taran, C. Gauchet, B. Mohar, S. Meunier, A. Valleix, P. Y. Renard, C. Créminon, I Grassi, A. Wagner, C. Mioskowski, Angew. Chem. 2002, 114, 132-135;
- (2002) Angew. Chem. , vol.114 , pp. 132-135
- Taran, F.¹ Gauchet, C.² Mohar, B.³ Meunier, S.⁴ Valleix, A.⁵ Renard, P.Y.⁶ Créminon, C.⁷ Grassi, I.⁸ Wagner, A.⁹ Mioskowski, C.¹⁰

49
- 0037016257
- Angew. Chem. Int. Ed. 2002, 41, 124-127;
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 124-127

50
- 20444408086
- b) D. Yang, X. Li, Y. F. Fan, D. W. Zhang, J. Am. Chem. Soc. 2005, 127, 7996-7997;
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 7996-7997
- Yang, D.¹ Li, X.² Fan, Y.F.³ Zhang, D.W.⁴

51
- 34547942528
- c) S. Shirakawa, A. Moriyama, S. Shimizu, Org. Lett. 2007, 9, 3117-3119.
- (2007) Org. Lett. , vol.9 , pp. 3117-3119
- Shirakawa, S.¹ Moriyama, A.² Shimizu, S.³

52
- 0037070577
- a) J. Lin, Q. S. Hu, M. H. Xu, L. Pu, J. Am. Chem. Soc. 2002, 124, 2088-2089;
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 2088-2089
- Lin, J.¹ Hu, Q.S.² Xu, M.H.³ Pu, L.⁴

53
- 0037184448
- b) M. H. Xu, J. Lin, Q. S. Hu, L. Pu, J. Am. Chem. Soc. 2002, 124, 14239-14246;
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 14239-14246
- Xu, M.H.¹ Lin, J.² Hu, Q.S.³ Pu, L.⁴

54
- 34250644054
- c) Z.-B. Li, J. Lin, L. Pu, Angew. Chem. 2005, 117, 1718-1721;
- (2005) Angew. Chem. , vol.117 , pp. 1718-1721
- Li, Z.-B.¹ Lin, J.² Pu, L.³

55
- 17044377598
- Angew. Chem. Int. Ed. 2005, 44, 1690-1693;
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 1690-1693

56
- 34250815078
- d) Z. B. Li, J. Lin, M. Sabat, M. Hyacinth, L. Pu, J. Org. Chem. 2007, 72, 4905-4916;
- (2007) J. Org. Chem. , vol.72 , pp. 4905-4916
- Li, Z.B.¹ Lin, J.² Sabat, M.³ Hyacinth, M.⁴ Pu, L.⁵

57
- 68149140550
- e) H. L. Liu, X. L. Hou, L. Pu, Angew. Chem. 2009, 121, 388-391;
- (2009) Angew. Chem. , vol.121 , pp. 388-391
- Liu, H.L.¹ Hou, X.L.² Pu, L.³

58
- 58249101193
- Angew. Chem. Int. Ed. 2009, 48, 382-385;
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 382-385

59
- 8844238341
- f) X. F. Mei, C. Wolf, J. Am. Chem. Soc. 2004, 126, 14736-14737;
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 14736-14737
- Mei, X.F.¹ Wolf, C.²

60
- 39649115795
- g) K. Dhara, K. Sarkar, P. Roy, M. Nandi, A. Bhaumik, P. Banerjee, Tetrahedron 2008, 64, 3153-3159.
- (2008) Tetrahedron , vol.64 , pp. 3153-3159
- Dhara, K.¹ Sarkar, K.² Roy, P.³ Nandi, M.⁴ Bhaumik, A.⁵ Banerjee, P.⁶

61
- 45249091691
- a) L. Chi, J. Z. Zhao, T. D. James, J. Org. Chem. 2008, 73, 4684-4687;
- (2008) J. Org. Chem. , vol.73 , pp. 4684-4687
- Chi, L.¹ Zhao, J.Z.² James, T.D.³

62
- 60649116676
- b) A. A. Williams, S. O. Fakayode, M. Lowry, I. M. Warner, Chirality 2009, 21, 305-315;
- (2009) Chirality , vol.21 , pp. 305-315
- Williams, A.A.¹ Fakayode, S.O.² Lowry, M.³ Warner, I.M.⁴

63
- 40549108998
- c) A. A. Williams, S. O. Fakayode, O. Alptürk, C. M. Jones, M. Lowry, R. M. Strongin, I. M. Warner, J. Fluoresc. 2008, 18, 285-296;
- (2008) J. Fluoresc. , vol.18 , pp. 285-296
- Williams, A.A.¹ Fakayode, S.O.² Alptürk, O.³ Jones, C.M.⁴ Lowry, M.⁵ Strongin, R.M.⁶ Warner, I.M.⁷

64
- 10344260928
- d)J. Z. Zhao, M. G. Davidson, M. F. Mahon, G. Kociok-Köhn, T. D. James, J. Am. Chem. Soc 2004, 126, 16179-16186.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 16179-16186
- Zhao, J.Z.¹ Davidson, M.G.² Mahon, M.F.³ Kociok-Köhn, G.⁴ James, T.D.⁵

65
- 74549131663
- CCDC 755118 ((S)-3) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
- CCDC 755118 ((S)-3) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.

66
- 74549171540
- The calculations were performed using a Gaussian 03 program: Gaussian03, revisionD.01, M.J. Frisch, et al., Gaussian, Inc., Wallingford, CT, 2004.
- The calculations were performed using a Gaussian 03 program: Gaussian03, revisionD.01, M.J. Frisch, et al., Gaussian, Inc., Wallingford, CT, 2004.

67
- 4243553426
- a) A. D. Becke, Phys Rev. A 1988, 38, 3098;
- (1988) Phys Rev. A , vol.38 , pp. 3098
- Becke, A.D.¹

68
- 34250817103
- b) A. D. Becke, J. Chem. Phys. 1993, 98, 1372;
- (1993) J. Chem. Phys. , vol.98 , pp. 1372
- Becke, A.D.¹

69
- 0000189651
- c) A. D. Becke, J. Chem. Phys. 1993, 98, 5648;
- (1993) J. Chem. Phys. , vol.98 , pp. 5648
- Becke, A.D.¹

70
- 0345491105
- d) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
- (1988) Phys. Rev. B , vol.37 , pp. 785
- Lee, C.¹ Yang, W.² Parr, R.G.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.