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

Mijoon Lee, Dusan Hesek, Bruce C. Noll, and Shahriar Mobashery

Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA

 

E-mail: mobashery@nd.edu

Received: 28 August 2008  Revised: 7 February 2009  Accepted: 26 February 2009

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

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-009-0048-0

 

Chemical Papers 63 (5) 592–597 (2009)

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