Dye-modified and photoswitchable macrocycles by multiple multicomponent macrocyclizations including bifunctional building blocks (MiBs)

QSAR and Combinatorial Science

Volumn 25, Issue 5-6, 2006, Pages 461-464

  Kreye, Oliver ^a   Westermann, Bernhard ^a   Rivera, Daniel G ^a   Johnson, Dean V ^b   Orru, Romano V A ^b   Wessjohann, Ludger A ^a  

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

^b VU UNIVERSITY AMSTERDAM   (Netherlands)

Author keywords

Dye; Macrocycle; Multicomponent reaction; Photoswitch

Indexed keywords

BI-FUNCTIONAL; BUILDING BLOCKES; MACRO-CYCLIZATION; MACROCYCLES; MULTICOMPONENT REACTION; MULTICOMPONENTS; PEPTOID; PHOTO-SWITCHABLE; PHOTOSWITCH;

CHEMICAL REACTIONS;

DYE; MACROCYCLIC COMPOUND;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; PRIORITY JOURNAL;

EID: 33745784582     PISSN: 1611020X     EISSN: 16110218     Source Type: Journal    
DOI: 10.1002/qsar.200540217     Document Type: Article

References (17)

1. a) L. A. Wessjohann, E. Ruijter, Mol. Divers. 2005, 9, 159.
2. b) L. A. Wessjohann, E. Ruijter, D. Garcia-Rivera, W. Brandt, Mol. Divers. 2005, 9, 171, and cited references.
3. J. Auernheimer, C. Dahmen, U. Hersel, A. Bausch, H. Kessler, J Am. Chem. Soc. 2005, 127, 16107, and cited references.
4. L. A. Wessjohann, B. Voigt, D. Garcia-Rivera, Angew. Chem. 2005, 117, 4863;
5. Angew. Chem. Int. Ed. 2005, 44, 4785.
6. a) Y. Ye, W. P. Li, C. J. Anderson, J. Kao, G. V. Nikiforovich, S. Achilefu, J. Am. Chem. Soc. 2003, 125, 7766.
7. b) Y. Ye, S. Bloch, S. Achilefeu, J. Am. Chem. Soc. 2004, 126, 7740.
8. D. Michalik, A. Schaks, L. A. Wessjohann, submitted.
9. D. L. Boger, S. L. Castle, "Synthesis of cycloisodityrosine peptides", in: Synthesis of Peptides and Peptidomimetics, Vol. E22c, M. Goodman et al. (Eds.), Thieme Medical, New York, 2002, p. 194: Houben-Weyl: Methods of Organic Chemistry, 4th edition and cited references.
10. a) R. S. Bon, B. van Vliet, N. E. Sprenkels, R. F. Schmitz, F. J. J. de Kanter, C. V. Stevens, M. Swart, F. M. Bickelhaupt, M. B. Groen, R. V. A. Orru, J. Org. Chem. 2005, 70, 3542.
11. b) R. V. A. Orru, M. de Greef, Synthesis 2003, 1471-1499.
12. G. J. Atwell, W. A. Denny, Synthesis, 1984, 1032.
13. 3, 62.8 MHz): δ (ppm) 17.21, 156.88, 156.68, 137.99, 137.13, 128.87, 128.44, 128.23, 127.98, 127.78, 126.75, 84.26, 67.74, 66.90, 53.21, 47.27, 47.15, 41.20, 30.20, 29.34, 28.67, 26.68, 23.22, 22.81, 16.52, 15.80. Cbz-deprotection can be achieved by catalytic hydrogenation with 20 wt.% palladium hydroxide on carbon in methanol overnight.
14. 3- (found).
15. H. Tian, S. Yang, Chem. Soc. Rev. 2004, 33, 85, and cited references.
16. a) A. Mulder, A. Jukovic, J. Huskens, D. N. Reinhoudt, Org. Bioorg. Chem. 2004, 2, 1748.
17. b) L. N. Lucas, J. J. D. de Jong, J. H. van Esch, R. M. Kellogg, B. L. Feringa, Eur. J. Org. Chem. 2003, 155.