RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
PDF herunterladen
Synthesis 2007(7): 1103-1106
DOI: 10.1055/s-2007-965945
DOI: 10.1055/s-2007-965945
PAPER
© Georg Thieme Verlag Stuttgart · New YorkSynthesis of Model Chromophores Related to the Gold Fluorescent Protein (GdFP)
Weitere Informationen
Received
19 January 2007
Publikationsdatum:
20. Februar 2007 (online)
Publikationsverlauf
Publikationsdatum:
20. Februar 2007 (online)
Abstract
The two model chromophores 2 and 3 for the core 1 of the gold fluorescent protein (GdFP) were synthesized from commercially available 2-methyl-3-nitroaniline (4) in six synthetic steps and overall yields of 13% and 8%, respectively. The key step of the sequence is the chemoselective, reductive introduction of the amino group after assembly of the Z-configured 5-(indol-3-ylmethylene)imidazolin-4-one skeleton of the chromophore. Compound (Z)-2 was shown to undergo a light-initiated E/Z-isomerization, which allows access also to its E-isomer.
Key words
aldol reactions - bioorganic chemistry - heterocycles - indoles - photochemistry
- Reviews:
- 1a
Zimmer M. Chem. Rev. 2002, 102: 759 - 1b
Tsien RY. Annu. Rev. Biochem. 1998, 67: 509 - Examples:
- 2a
Ehrhardt E. Curr. Opin. Plant Biol. 2003, 6: 622 - 2b
Chudakov DM.Lukyanov KA. Biochemistry (Moscow) 2003, 68: 952 - 2c
Michaelson D.Philips M. Methods Enzymol. 2000, 406: 296 - 2d
Prasher DC. Trends Genet. 1995, 11: 320 - 3a
Shimomura O. FEBS Lett. 1979, 104: 220 - 3b
Cody CW.Prasher DC.Westler WM.Prendergast FG.Ward WW. Biochemistry 1993, 32: 1212 - 3c
Reid BG.Flynn GC. Biochemistry 1997, 36: 6786 - Examples:
- 4a
Kojima S.Ohkawa H.Hirano T.Maki S.Niwa H.Ohashi M.Inouye S.Tsuji FI. Tetrahedron Lett. 1998, 39: 5239 - 4b
He X.Bell AF.Tonge PJ. Org. Lett. 2002, 4: 1523 - 4c
Yampolsky IV.Remington SJ.Martynov VI.Potapov VK.Lukyanov S.Lukyanov KA. Biochemistry 2005, 44: 5788 - 4d
Hager B.Schwarzinger B.Falk H. Monatsh. Chem. 2006, 137: 163 - 5
Bae JH.Rubini M.Jung G.Wiegand G.Seifert MHJ.Azim MK.Kim J.-S.Zumbusch A.Holak TA.Moroder L.Huber R.Budisa N. J. Mol. Biol. 2003, 328: 1071 - 6a
Budisa N.Rubini M.Bae JH.Weyher E.Wenger W.Golbik R.Huber R.Moroder L. Angew. Chem. Int. Ed. 2002, 41: 4066 - 6b
Budisa N. ChemBioChem 2004, 5: 1176 - 6c
Budisa N.Pal PP. Biol. Chem. 2004, 385: 893 - 7a
Erlenmeyer E. Liebigs Ann. Chem. 1893, 275: 1 - 7b
Erlenmeyer E.Früstück E. Liebigs Ann. Chem. 1895, 284: 36 - Reviews:
- 8a
Rosen T. In Comprehensive Organic Synthesis Vol. 2:Trost B.Fleming I.Heacthcock CH. Pergamon; Oxford: 1991. p.395-408 - 8b
Mukerjee AK. Heterocycles 1987, 26: 1077 - 8c
Mukerjee AK.Kumar P. Heterocycles 1981, 16: 1995 - 8d
Filler R. Adv. Heterocycl. Chem. 1965, 4: 75 - 8e
Cornforth JW. In Heterocyclic Compounds Vol. 5:Elderfield RC. Wiley; New York: 1957. p.298-417 - 8f
Baltazzi E. Q. Rev. Chem. Soc. 1955, 9: 150 - 8g
Cornforth JW. In Chemistry of PenicillinClarke HT.Johnson JR.Robinson R. Princeton University Press; Princeton, N. J.: 1948. p.688-848 - 8h
Carter HE. Org. React. 1947, 3: 198 - 9a
Ojima I.Kato K.Nakahashi K.Fuchikami T.Fujita M. J. Org. Chem. 1989, 54: 4511 - 9b
Oba M.Ueno R.Fukuoka M.Kainosho M.Nishiyama K. J. Chem. Soc., Perkin Trans. 1 1995, 1603 - 9c
Donati D.Garzon-Aburbeh A.Natalini B.Marchioro C.Pellicciari R. Tetrahedron 1996, 52: 9901 - 9d
Mesaik MA.Rahat S.Khan KM. .Choudhary MI.Murad S.Ismail Z. .Ahmad A. Bioorg. Med. Chem. 2004, 12: 2049 - 9e
Guella G.N’Diaye I.Fofana M.Marcini I. Tetrahedron 2006, 62: 1165 - 10a
Erlenmeyer E.Wittenberg F. Liebigs Ann. Chem. 1904, 337: 294 - 10b
Narang KS.Ray JN. J. Chem. Soc. 1931, 976 - 10c
Williams DL.Ronzio AR. J. Am. Chem. Soc. 1946, 68: 647 - 10d
Pfleger R.Markert G. Chem. Ber. 1957, 90: 1494 - 11a
Bergman J.Sand P. Org. Synth. 1987, 65: 146 - 11b
Melhado LL.Brodsky JL. J. Org. Chem. 1988, 53: 3852 - 11c
Bergman J.Sand P. Tetrahedron 1990, 46: 6085 - 12
Rao YS.Filler R. Synthesis 1975, 749 - 13a
Byk G.Gilon C. J. Org. Chem. 1992, 57: 5687 - 13b
Muller D.Zeltser I.Bitan G.Gilon C. J. Org. Chem. 1997, 62: 411 - 13c
Pons J.-F.Fauchière J.-L.Lamaty F.Molla A.Lazaro R. Eur. J. Org. Chem. 1998, 853 - 14
Herbst RM.Shemin D. Org. Synth. Coll. Vol. II Wiley; New York: 1943. p.11-12Reference Ris Wihthout Link