ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
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
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.
Chemical Papers 63 (5) 592–597 (2009)