Synthesis 2008(8): 1316-1318  
DOI: 10.1055/s-2008-1032016
PSP
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 4-Maleimidobutyric Acid and Related Maleimides

Renata Marcia de Figueiredoa, Philipp Oczipkaa, Roland Fröhlichb, Mathias Christmann*a
a Institute of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany
b Institute of Organic Chemistry, University of Münster, Corrensstraße 40, 48149 Münster, Germany
Fax: +49(241)8092127; e-Mail: [email protected];
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Publikationsverlauf

Received 12 September 2007
Publikationsdatum:
10. Januar 2008 (online)

Abstract

Maleimidoalkanoic acids and their activated derivatives, such as their N-hydroxysuccinimide esters, are important, though expensive, linkers for the conjugation of biomolecules. During our synthesis of UCS1025A, we have developed a chromatography-free preparation of 4-maleimidobutyric acid on a one-mole scale.

    References

  • 1 Rich DH. Gesellchen PD. Tong A. Cheung A. Buckner CK. J. Med. Chem.  1975,  18:  1004 
  • 2a Stuhlmann F. Jäschke A. J. Am. Chem. Soc.  2002,  124:  3238 
  • 2b Herrmann A. Mihov G. Vandermeulen GWM. Klok H.-A. Müllen K. Tetrahedron  2003,  59:  3925 
  • 2c Bennes RM. Philp D. Org. Lett.  2006,  8:  3651 
  • 2d de Araújo AD. Palomo JM. Cramer J. Seitz O. Alexandrov K. Waldmann H. Chem. Eur. J.  2006,  12:  6095 
  • 2e Meyer-Losic F. Quinonero J. Dubois V. Alluis B. Dechambre M. Michel M. Cailler F. Fernandez A.-M. Trouet A. Kearsey J. J. Med. Chem.  2006,  49:  6908 
  • 3 Lambert TH. Danishefsky SJ. J. Am. Chem. Soc.  2006,  128:  426 
  • 4 Hoye TR. Dvornikovs V. J. Am. Chem. Soc.  2006,  128:  2550 
  • 5a Nakai R. Ogawa H. Asai A. Ando K. Agatsuma T. Matsumiya S. Akinaga S. Yamashita Y. Mizukami T. J. Antibiot.  2000,  53:  294 
  • 5b Agatsuma T. Akama T. Nara S. Matsumiya S. Nakai R. Ogawa H. Otaki S. Ikeda S.-i. Saitoh Y. Kanda Y. Org. Lett.  2002,  4:  4387 
  • 5c Nakai R. Ishida H. Asai A. Ogawa H. Yamamoto Y. Kawasaki H. Akinaga S. Mizukami T. Yamashita Y. Chem. Biol.  2006,  13:  183 
  • 6a de Figueiredo RM. Fröhlich R. Christmann M. Angew. Chem. Int. Ed.  2007,  46:  2883 
  • 6b de Figueiredo RM. Voith M. Fröhlich R. Christmann M. Synlett  2007,  391 
  • 7a Mantovani G. Lecolley F. Tao L. Haddleton DM. Clerx J. Cornelissen JJLM. Velonia K. J. Am. Chem. Soc.  2005,  127:  2966 
  • 7b Lavis LD. Chao T. Raines RT. ACS Chem. Biol.  2006,  1:  252 
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