Fluorescent detection of carbon-carbon bond formation

Journal of the American Chemical Society

Volumn 125, Issue 28, 2003, Pages 8523-8528

  Tanaka, Fujie ^a   Thayumanavan, Rajeswari ^a   Barbas III, Carlos F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUOROPHORES;

APPROXIMATION THEORY; CATALYSTS; FLUORESCENCE; SUBSTRATES;

CHEMICAL BONDS;

CARBON; CARBONYL DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL BINDING; CHEMICAL BOND; DIELS ALDER REACTION; FLUORESCENCE; MICHAEL ADDITION; REACTION ANALYSIS;

ACETONE; AMIDES; AMINES; AMINO ACID SEQUENCE; FRUCTOSE-BISPHOSPHATE ALDOLASE; MOLECULAR SEQUENCE DATA; ORGANIC CHEMICALS; PEPTIDE FRAGMENTS; SPECTROMETRY, FLUORESCENCE;

EID: 0038375490     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034069t     Document Type: Article

References (61)

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12. (a) Fluorescence-based assay for C-C bond formation using a solid support: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (b) C-C bond formation based on fluorescence resonance energy transfer: Stauffer, S. R.; Beare, N. A.; Stambuli, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4641. Because decreases in fluorescence were monitored, an aliquot from the reaction mixture was diluted, and the yield was determined after a measurable amount of the product was generated (> 10%). (c) Examples of spectroscopic and visual catalyst screening for bond forming reactions (other than C-C bond formation): Cooper, A. C.; McAlexander, L. H.; Lee, D.-H.; Torres, M. T.; Crabtree, R. H. J. Am. Chem. Soc. 1998, 120, 9971. Taylor, S. J.; Morken, J. P. Science 1998, 280, 267. Reetz, M. T.; Becker, M. H.; Kuhling, K. M.; Holzwarth, A. Angew. Chem., Int. Ed. 1998, 37, 2647. Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 4306. Harris, R. F.; Nation, A. J.; Copland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2000, 122, 11270. Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. Francis, M. B.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 937. Yeung, E. S.; Su, H. J. Am. Chem. Soc. 2000, 122, 7422.
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15. (a) Fluorescence-based assay for C-C bond formation using a solid support: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (b) C-C bond formation based on fluorescence resonance energy transfer: Stauffer, S. R.; Beare, N. A.; Stambuli, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4641. Because decreases in fluorescence were monitored, an aliquot from the reaction mixture was diluted, and the yield was determined after a measurable amount of the product was generated (> 10%). (c) Examples of spectroscopic and visual catalyst screening for bond forming reactions (other than C-C bond formation): Cooper, A. C.; McAlexander, L. H.; Lee, D.-H.; Torres, M. T.; Crabtree, R. H. J. Am. Chem. Soc. 1998, 120, 9971. Taylor, S. J.; Morken, J. P. Science 1998, 280, 267. Reetz, M. T.; Becker, M. H.; Kuhling, K. M.; Holzwarth, A. Angew. Chem., Int. Ed. 1998, 37, 2647. Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 4306. Harris, R. F.; Nation, A. J.; Copland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2000, 122, 11270. Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. Francis, M. B.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 937. Yeung, E. S.; Su, H. J. Am. Chem. Soc. 2000, 122, 7422.
16. (a) Fluorescence-based assay for C-C bond formation using a solid support: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (b) C-C bond formation based on fluorescence resonance energy transfer: Stauffer, S. R.; Beare, N. A.; Stambuli, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4641. Because decreases in fluorescence were monitored, an aliquot from the reaction mixture was diluted, and the yield was determined after a measurable amount of the product was generated (> 10%). (c) Examples of spectroscopic and visual catalyst screening for bond forming reactions (other than C-C bond formation): Cooper, A. C.; McAlexander, L. H.; Lee, D.-H.; Torres, M. T.; Crabtree, R. H. J. Am. Chem. Soc. 1998, 120, 9971. Taylor, S. J.; Morken, J. P. Science 1998, 280, 267. Reetz, M. T.; Becker, M. H.; Kuhling, K. M.; Holzwarth, A. Angew. Chem., Int. Ed. 1998, 37, 2647. Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 4306. Harris, R. F.; Nation, A. J.; Copland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2000, 122, 11270. Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. Francis, M. B.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 937. Yeung, E. S.; Su, H. J. Am. Chem. Soc. 2000, 122, 7422.
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25. Examples of amine-catalyzed Michael reactions of carbonyl compounds: Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176. Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. Bui, T.; Barbas, C. F., III. Tetrahedron Lett. 2000, 41, 6951. Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737. Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441. List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. Enders, D.; Seki, A. Synlett 2002, 26. Halland, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 8331. Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192. Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661.
26. Examples of amine-catalyzed Michael reactions of carbonyl compounds: Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176. Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. Bui, T.; Barbas, C. F., III. Tetrahedron Lett. 2000, 41, 6951. Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737. Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441. List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. Enders, D.; Seki, A. Synlett 2002, 26. Halland, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 8331. Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192. Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661.
27. Examples of amine-catalyzed Michael reactions of carbonyl compounds: Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176. Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. Bui, T.; Barbas, C. F., III. Tetrahedron Lett. 2000, 41, 6951. Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737. Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441. List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. Enders, D.; Seki, A. Synlett 2002, 26. Halland, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 8331. Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192. Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661.
28. Examples of amine-catalyzed Michael reactions of carbonyl compounds: Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176. Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. Bui, T.; Barbas, C. F., III. Tetrahedron Lett. 2000, 41, 6951. Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737. Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441. List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. Enders, D.; Seki, A. Synlett 2002, 26. Halland, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 8331. Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192. Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661.
29. Examples of amine-catalyzed Michael reactions of carbonyl compounds: Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176. Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. Bui, T.; Barbas, C. F., III. Tetrahedron Lett. 2000, 41, 6951. Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737. Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441. List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. Enders, D.; Seki, A. Synlett 2002, 26. Halland, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 8331. Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192. Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661.
30. Examples of amine-catalyzed Michael reactions of carbonyl compounds: Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176. Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. Bui, T.; Barbas, C. F., III. Tetrahedron Lett. 2000, 41, 6951. Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737. Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441. List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. Enders, D.; Seki, A. Synlett 2002, 26. Halland, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 8331. Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192. Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661.
31. Examples of amine-catalyzed Michael reactions of carbonyl compounds: Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176. Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. Bui, T.; Barbas, C. F., III. Tetrahedron Lett. 2000, 41, 6951. Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737. Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441. List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. Enders, D.; Seki, A. Synlett 2002, 26. Halland, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 8331. Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192. Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661.
32. Examples of amine-catalyzed Michael reactions of carbonyl compounds: Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176. Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. Bui, T.; Barbas, C. F., III. Tetrahedron Lett. 2000, 41, 6951. Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737. Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441. List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. Enders, D.; Seki, A. Synlett 2002, 26. Halland, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 8331. Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192. Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661.
33. Examples of amine-catalyzed Michael reactions of carbonyl compounds: Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176. Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. Bui, T.; Barbas, C. F., III. Tetrahedron Lett. 2000, 41, 6951. Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737. Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441. List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. Enders, D.; Seki, A. Synlett 2002, 26. Halland, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 8331. Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192. Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661.
34. Examples of amine-catalyzed Michael reactions of carbonyl compounds: Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176. Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. Bui, T.; Barbas, C. F., III. Tetrahedron Lett. 2000, 41, 6951. Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737. Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441. List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. Enders, D.; Seki, A. Synlett 2002, 26. Halland, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 8331. Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192. Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661.
35. Examples of amine-catalyzed Michael reactions of carbonyl compounds: Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176. Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. Bui, T.; Barbas, C. F., III. Tetrahedron Lett. 2000, 41, 6951. Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737. Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441. List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. Enders, D.; Seki, A. Synlett 2002, 26. Halland, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 8331. Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192. Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661.
36. Examples of amine-catalyzed Michael reactions of carbonyl compounds: Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176. Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. Bui, T.; Barbas, C. F., III. Tetrahedron Lett. 2000, 41, 6951. Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737. Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441. List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. Enders, D.; Seki, A. Synlett 2002, 26. Halland, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 8331. Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192. Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661.
37. Examples of amine-catalyzed Michael reactions of carbonyl compounds: Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176. Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. Bui, T.; Barbas, C. F., III. Tetrahedron Lett. 2000, 41, 6951. Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737. Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441. List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. Enders, D.; Seki, A. Synlett 2002, 26. Halland, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 8331. Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192. Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661.
38. Examples of amine-catalyzed Michael reactions of carbonyl compounds: Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176. Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. Bui, T.; Barbas, C. F., III. Tetrahedron Lett. 2000, 41, 6951. Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737. Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441. List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. Enders, D.; Seki, A. Synlett 2002, 26. Halland, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 8331. Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192. Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661.
39. Examples of amine-catalyzed Michael reactions of carbonyl compounds: Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176. Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. Bui, T.; Barbas, C. F., III. Tetrahedron Lett. 2000, 41, 6951. Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737. Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441. List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. Enders, D.; Seki, A. Synlett 2002, 26. Halland, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 8331. Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192. Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661.
40. Fluorescence spectra were recorded on Spectra Max Gemini (Molecular Devices) using 100 μL of the solution in a 96-well plate (Costar 3915) at 25 °C. The data are shown after background correction.
41. (a) Tanaka, F.; Barbas, C. F., III. Chem. Commun. 2001, 769.
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47. Hydrolysis of 1 to generate 4-(1H-benzimidazol-2-yl)aniline, a fluorophore, contributes to an increase of fluorescence in the background reaction. In the HPLC assay of these reactions without antibody (background) and with nonaldolase antibody (control), no generation of 2 was detected (below the detection limit).
48. Thayumanavan, R.; Dhevalapally, B.; Sakthivel, K.; Tanaka, F.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 3817. Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 6743.
49. Thayumanavan, R.; Dhevalapally, B.; Sakthivel, K.; Tanaka, F.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 3817. Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 6743.
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51. The fluorescence emission of 6-aminoquinoline is 400-650 nm (ref 11 and Supporting Information). When the formation of 6 is detected by fluorescence measurement at emission wavelengths shorter than 390 nm, the increase in fluorescence can exclude the effect of 6-aminoquinoline that may be generated by aryl amide hydrolysis of 5 in buffer.
52. Examples of catalysts of C-C bond formation selected from libraries. Catalytic antibodies: refs 2a, 2e, 8a. Zhong, G.; Lerner, R. A.; Barbas, C. F., III. Angew. Chem., Int. Ed. 1999, 38, 3738. Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261. Braisted, A.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 7430. Gouveneur, V. E.; Houk, K. N.; Pascual-Teresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204. RNA catalysts: Morris, K. N.; Tarasow, T. M.; Julin, C. M.; Simons, S. L.; Hilvert, D.; Gold, L. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 13028. Tarasow, T. M.; Tarasow, S. L.; Eaton, B. E. Nature 1997, 389, 54. Seelig, B.; Jaschke, A. Chem. Biol. 1999, 6, 167. Tarasow, T. M.; Tarasow, S. L.; Eaton, B. E. J. Am. Chem. Soc. 2000, 122, 1015. Mielcarek, M.; Barciszewska, M. Z.; Salanski, P.; Stobiecki, M.; Jurczak, J.; Barciszewski, J. Biochem. Biophys. Res. Commun. 2002, 294, 145.
53. Examples of catalysts of C-C bond formation selected from libraries. Catalytic antibodies: refs 2a, 2e, 8a. Zhong, G.; Lerner, R. A.; Barbas, C. F., III. Angew. Chem., Int. Ed. 1999, 38, 3738. Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261. Braisted, A.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 7430. Gouveneur, V. E.; Houk, K. N.; Pascual-Teresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204. RNA catalysts: Morris, K. N.; Tarasow, T. M.; Julin, C. M.; Simons, S. L.; Hilvert, D.; Gold, L. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 13028. Tarasow, T. M.; Tarasow, S. L.; Eaton, B. E. Nature 1997, 389, 54. Seelig, B.; Jaschke, A. Chem. Biol. 1999, 6, 167. Tarasow, T. M.; Tarasow, S. L.; Eaton, B. E. J. Am. Chem. Soc. 2000, 122, 1015. Mielcarek, M.; Barciszewska, M. Z.; Salanski, P.; Stobiecki, M.; Jurczak, J.; Barciszewski, J. Biochem. Biophys. Res. Commun. 2002, 294, 145.
54. Examples of catalysts of C-C bond formation selected from libraries. Catalytic antibodies: refs 2a, 2e, 8a. Zhong, G.; Lerner, R. A.; Barbas, C. F., III. Angew. Chem., Int. Ed. 1999, 38, 3738. Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261. Braisted, A.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 7430. Gouveneur, V. E.; Houk, K. N.; Pascual-Teresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204. RNA catalysts: Morris, K. N.; Tarasow, T. M.; Julin, C. M.; Simons, S. L.; Hilvert, D.; Gold, L. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 13028. Tarasow, T. M.; Tarasow, S. L.; Eaton, B. E. Nature 1997, 389, 54. Seelig, B.; Jaschke, A. Chem. Biol. 1999, 6, 167. Tarasow, T. M.; Tarasow, S. L.; Eaton, B. E. J. Am. Chem. Soc. 2000, 122, 1015. Mielcarek, M.; Barciszewska, M. Z.; Salanski, P.; Stobiecki, M.; Jurczak, J.; Barciszewski, J. Biochem. Biophys. Res. Commun. 2002, 294, 145.
55. Examples of catalysts of C-C bond formation selected from libraries. Catalytic antibodies: refs 2a, 2e, 8a. Zhong, G.; Lerner, R. A.; Barbas, C. F., III. Angew. Chem., Int. Ed. 1999, 38, 3738. Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261. Braisted, A.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 7430. Gouveneur, V. E.; Houk, K. N.; Pascual-Teresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204. RNA catalysts: Morris, K. N.; Tarasow, T. M.; Julin, C. M.; Simons, S. L.; Hilvert, D.; Gold, L. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 13028. Tarasow, T. M.; Tarasow, S. L.; Eaton, B. E. Nature 1997, 389, 54. Seelig, B.; Jaschke, A. Chem. Biol. 1999, 6, 167. Tarasow, T. M.; Tarasow, S. L.; Eaton, B. E. J. Am. Chem. Soc. 2000, 122, 1015. Mielcarek, M.; Barciszewska, M. Z.; Salanski, P.; Stobiecki, M.; Jurczak, J.; Barciszewski, J. Biochem. Biophys. Res. Commun. 2002, 294, 145.
56. Examples of catalysts of C-C bond formation selected from libraries. Catalytic antibodies: refs 2a, 2e, 8a. Zhong, G.; Lerner, R. A.; Barbas, C. F., III. Angew. Chem., Int. Ed. 1999, 38, 3738. Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261. Braisted, A.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 7430. Gouveneur, V. E.; Houk, K. N.; Pascual-Teresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204. RNA catalysts: Morris, K. N.; Tarasow, T. M.; Julin, C. M.; Simons, S. L.; Hilvert, D.; Gold, L. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 13028. Tarasow, T. M.; Tarasow, S. L.; Eaton, B. E. Nature 1997, 389, 54. Seelig, B.; Jaschke, A. Chem. Biol. 1999, 6, 167. Tarasow, T. M.; Tarasow, S. L.; Eaton, B. E. J. Am. Chem. Soc. 2000, 122, 1015. Mielcarek, M.; Barciszewska, M. Z.; Salanski, P.; Stobiecki, M.; Jurczak, J.; Barciszewski, J. Biochem. Biophys. Res. Commun. 2002, 294, 145.
57. Examples of catalysts of C-C bond formation selected from libraries. Catalytic antibodies: refs 2a, 2e, 8a. Zhong, G.; Lerner, R. A.; Barbas, C. F., III. Angew. Chem., Int. Ed. 1999, 38, 3738. Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261. Braisted, A.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 7430. Gouveneur, V. E.; Houk, K. N.; Pascual-Teresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204. RNA catalysts: Morris, K. N.; Tarasow, T. M.; Julin, C. M.; Simons, S. L.; Hilvert, D.; Gold, L. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 13028. Tarasow, T. M.; Tarasow, S. L.; Eaton, B. E. Nature 1997, 389, 54. Seelig, B.; Jaschke, A. Chem. Biol. 1999, 6, 167. Tarasow, T. M.; Tarasow, S. L.; Eaton, B. E. J. Am. Chem. Soc. 2000, 122, 1015. Mielcarek, M.; Barciszewska, M. Z.; Salanski, P.; Stobiecki, M.; Jurczak, J.; Barciszewski, J. Biochem. Biophys. Res. Commun. 2002, 294, 145.
58. Examples of catalysts of C-C bond formation selected from libraries. Catalytic antibodies: refs 2a, 2e, 8a. Zhong, G.; Lerner, R. A.; Barbas, C. F., III. Angew. Chem., Int. Ed. 1999, 38, 3738. Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261. Braisted, A.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 7430. Gouveneur, V. E.; Houk, K. N.; Pascual-Teresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204. RNA catalysts: Morris, K. N.; Tarasow, T. M.; Julin, C. M.; Simons, S. L.; Hilvert, D.; Gold, L. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 13028. Tarasow, T. M.; Tarasow, S. L.; Eaton, B. E. Nature 1997, 389, 54. Seelig, B.; Jaschke, A. Chem. Biol. 1999, 6, 167. Tarasow, T. M.; Tarasow, S. L.; Eaton, B. E. J. Am. Chem. Soc. 2000, 122, 1015. Mielcarek, M.; Barciszewska, M. Z.; Salanski, P.; Stobiecki, M.; Jurczak, J.; Barciszewski, J. Biochem. Biophys. Res. Commun. 2002, 294, 145.
59. Examples of catalysts of C-C bond formation selected from libraries. Catalytic antibodies: refs 2a, 2e, 8a. Zhong, G.; Lerner, R. A.; Barbas, C. F., III. Angew. Chem., Int. Ed. 1999, 38, 3738. Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261. Braisted, A.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 7430. Gouveneur, V. E.; Houk, K. N.; Pascual-Teresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204. RNA catalysts: Morris, K. N.; Tarasow, T. M.; Julin, C. M.; Simons, S. L.; Hilvert, D.; Gold, L. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 13028. Tarasow, T. M.; Tarasow, S. L.; Eaton, B. E. Nature 1997, 389, 54. Seelig, B.; Jaschke, A. Chem. Biol. 1999, 6, 167. Tarasow, T. M.; Tarasow, S. L.; Eaton, B. E. J. Am. Chem. Soc. 2000, 122, 1015. Mielcarek, M.; Barciszewska, M. Z.; Salanski, P.; Stobiecki, M.; Jurczak, J.; Barciszewski, J. Biochem. Biophys. Res. Commun. 2002, 294, 145.
60. Examples of catalysts of C-C bond formation selected from libraries. Catalytic antibodies: refs 2a, 2e, 8a. Zhong, G.; Lerner, R. A.; Barbas, C. F., III. Angew. Chem., Int. Ed. 1999, 38, 3738. Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261. Braisted, A.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 7430. Gouveneur, V. E.; Houk, K. N.; Pascual-Teresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204. RNA catalysts: Morris, K. N.; Tarasow, T. M.; Julin, C. M.; Simons, S. L.; Hilvert, D.; Gold, L. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 13028. Tarasow, T. M.; Tarasow, S. L.; Eaton, B. E. Nature 1997, 389, 54. Seelig, B.; Jaschke, A. Chem. Biol. 1999, 6, 167. Tarasow, T. M.; Tarasow, S. L.; Eaton, B. E. J. Am. Chem. Soc. 2000, 122, 1015. Mielcarek, M.; Barciszewska, M. Z.; Salanski, P.; Stobiecki, M.; Jurczak, J.; Barciszewski, J. Biochem. Biophys. Res. Commun. 2002, 294, 145.
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