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Chemical Papers

, Volume 63, Issue 5, pp 592–597 | Cite as

Key side products due to reactivity of dimethylmaleoyl moiety as amine protective group

  • Mijoon Lee
  • Dusan Hesek
  • Bruce C. Noll
  • Shahriar MobasheryEmail author
Original Paper

Abstract

Dimethylmaleoyl (DMM) moiety has become an important amine protective group in sugar chemistry. We disclose herein that DMM-containing D-glucosamine analogues, because of their electrophilic nature, are prone to reactions with strong nucleophiles, such as hydrazine, resulting in a set of undesired side products that are difficult to detect, yet proved to be problematic for organic synthesis.

Keywords

amine protective group dimethylmaleoyl glucosamine carbohydrate peptidoglycan 

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References

  1. Aly, M. R. E., Castro-Palomino, J. C., Ibrahim, E. S. I., El-Ashry, E. S. H., & Schmidt, R. R. (1998). The dimethylmaleoyl group as amino protective group — application to the synthesis of glucosamine-containing oligosaccharides. European Journal of Organic Chemistry, 2305–2316. DOI: 10.1002/(SICI)1099-0690(199811)1998:11〈2305:AID-EJOC2305〉3.0.CO;2-W.Google Scholar
  2. Aly, M. R. E., Ibrahim, E. S. I., El Ashry, E. S. H., & Schmidt, R. R. (2001). Synthesis of chitotetraose and chitohexaose based on dimethylmaleoyl protection. Carbohydrate Research, 331, 129–142. DOI: 10.1016/S0008-6215(01)00024-6.CrossRefGoogle Scholar
  3. Bruker. (2008). Apex2 [computer software]. Madison, WI: Bruker AXS Inc.Google Scholar
  4. Cho, S., Wang, Q., Swaminathan, C. P., Hesek, D., Lee, M., Boons, G. J., Mobashery, S., & Mariuzza, R. A. (2007). Structural insights into the bactericidal mechanism of human peptidoglycan recognition proteins. Proceedings of the National Academy of Sciences of the United States of America, 104,8761–8766. DOI: 10.1073/pnas.0701453104.CrossRefGoogle Scholar
  5. El Ashry, E. S. H., & Aly, M. R. E. (2007). Synthesis and biological relevance of N-acetylglucosamine-containing oligosaccharides. Pure and Applied Chemistry, 79, 2229–2242. DOI: 10.1351/pac200779122229.CrossRefGoogle Scholar
  6. Fuda, C., Hesek, D., Lee, M., Morio, K.-I., Nowak, T., & Mobashery, S. (2005). Activation for catalysis of penicillinbinding protein 2a from methicillin-resistant Staphylococcus aureus by bacterial cell wall. Journal of the American Chemical Society, 127, 2056–2057. DOI: 10.1021/ja0434376.CrossRefGoogle Scholar
  7. Hedaya, E., Hinman, R. L., & Theodoropulos, S. (1966). Preparation and properties of some new N,N′-biisoimides and their cyclic isomers. Reaction of N,N′-biisomaleimide with dienes. Journal of Organic Chemistry, 31, 1317–1326. DOI: 10.1021/jo01343a002.CrossRefGoogle Scholar
  8. Hesek, D., Lee, M., Morio, K.-I., & Mobashery, S. (2004a). Synthesis of a fragment of bacterial cell wall. Journal of Organic Chemistry, 69, 2137–2146. DOI: 10.1021/jo035583k.CrossRefGoogle Scholar
  9. Hesek, D., Suvorov, M., Morio, K.-I., Lee, M., Brown, S., Vakulenko, S. B., & Mobashery, S. (2004b). Synthetic peptidoglycan substrates for penicillin-binding protein 5 of gramnegative bacteria. Journal of Organic Chemistry, 69, 778–784. DOI: 10.1021/jo035397e.CrossRefGoogle Scholar
  10. Horning, R. H., & Amstutz, E. D. (1955). The preparation of some dialkyl pyridazines. Journal of Organic Chemistry, 20, 707–713. DOI: 10.1021/jo01124a003.CrossRefGoogle Scholar
  11. Meroueh, S. O., Bencze, K. Z., Hesek, D., Lee, M., Fisher, J. F., Stemmler, T. L., & Mobashery, S. (2006). Three-dimensional structure of the bacterial cell wall peptidoglycan. Proceedings of the National Academy of Sciences of the United States of America, 103, 4404–4409. DOI: 10.1073/pnas.0510182103.CrossRefGoogle Scholar
  12. Perez-Dorado, I., Campillo, N. E., Monterroso, B., Hesek, D., Lee, M., Paez, J. A., Garcia, P., Martinez-Ripoll, M., Garcia, J. L., Mobashery, S., Menendez, M., & Hermoso, J. A. (2007). Elucidation of the molecular recognition of bacterial cell wall by modular pneumococcal phage endolysin CPL-1. Journal of Biological Chemistry, 282, 24990–24999. DOI: 10.1074/jbc.M704317200.CrossRefGoogle Scholar
  13. Sheldrick, G. M. (2008). A short history of SHELX. Acta Crystallographica Section A, 64, 112–122. DOI: 10.1107/S0108767307043930.CrossRefGoogle Scholar
  14. Steck, E. A., Brundage, R. P., & Fletcher, L. T. (1954). Pyridazine derivatives. 3. Some 3,6-disubstituted pyridazines having neuromuscular blocking activity. Journal of the American Chemical Society, 76, 4454–4457. DOI: 10.1021/ja01646a050.CrossRefGoogle Scholar

Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2009

Authors and Affiliations

  • Mijoon Lee
    • 1
  • Dusan Hesek
    • 1
  • Bruce C. Noll
    • 1
  • Shahriar Mobashery
    • 1
    Email author
  1. 1.Department of Chemistry and BiochemistryUniversity of Notre DameNotre DameUSA

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