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


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.


amine protective group dimethylmaleoyl glucosamine carbohydrate peptidoglycan 


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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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