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.
[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. Search in 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. http://dx.doi.org/10.1016/S0008-6215(01)00024-610.1016/S0008-6215(01)00024-6Search in Google Scholar
[3] Bruker. (2008). Apex2 [computer software]. Madison, WI: Bruker AXS Inc. Search in 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. http://dx.doi.org/10.1073/pnas.070145310410.1073/pnas.0701453104Search in Google Scholar PubMed PubMed Central
[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. http://dx.doi.org/10.1351/pac20077912222910.1351/pac200779122229Search in Google 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. http://dx.doi.org/10.1021/ja043437610.1021/ja0434376Search in Google Scholar PubMed
[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. http://dx.doi.org/10.1021/jo01343a00210.1021/jo01343a002Search in Google 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. http://dx.doi.org/10.1021/jo035583k10.1021/jo035583kSearch in Google Scholar PubMed
[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. http://dx.doi.org/10.1021/jo035397e10.1021/jo035397eSearch in Google Scholar PubMed
[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. http://dx.doi.org/10.1021/jo01124a00310.1021/jo01124a003Search in Google 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. http://dx.doi.org/10.1073/pnas.051018210310.1073/pnas.0510182103Search in Google Scholar PubMed PubMed Central
[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. http://dx.doi.org/10.1074/jbc.M70431720010.1074/jbc.M704317200Search in Google Scholar PubMed
[13] Sheldrick, G. M. (2008). A short history of SHELX. Acta Crystallographica Section A, 64, 112–122. DOI: 10.1107/S0108767307043930. http://dx.doi.org/10.1107/S010876730704393010.1107/S0108767307043930Search in Google Scholar PubMed
[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. http://dx.doi.org/10.1021/ja01646a05010.1021/ja01646a050Search in Google Scholar
© 2009 Institute of Chemistry, Slovak Academy of Sciences
Articles in the same Issue
- Magnetic nano- and microparticles in biotechnology
- Application of gas chromatography-mass spectrometry in research of traditional Chinese medicine
- Copper determination using ICP-MS with hexapole collision cell
- Reactivation of a palladium catalyst during glucose oxidation by molecular oxygen
- Robust stabilization of a chemical reactor
- Influence of production progress on the heavy metal content in flax fibers
- In vitro antifungal and antibacterial properties of thiodiamine transition metal complexes
- Synthesis, characterization, and antimicrobial activity of new benzoylthiourea ligands
- Investigation of DNA cleavage activities of new oxime-type ligand complexes and molecular modeling of complex-DNA interactions
- Characterization of mechanochemically synthesized lead selenide
- Hydroxyapatite modified with silica used for sorption of copper(II)
- Corrosion resistance of zinc electrodeposited from acidic and alkaline electrolytes using pulse current
- Ternary composites of multi-wall carbon nanotubes, polyaniline, and noble-metal nanoparticles for potential applications in electrocatalysis
- Synthesis of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine derivatives
- Key side products due to reactivity of dimethylmaleoyl moiety as amine protective group
- Comparative DFT study on the α-glycosidic bond in reactive species of galactosyl diphosphates
- Gas chromatographic retention times prediction for components of petroleum condensate fraction
- Gas chromatography with surface ionization detection of nitro pesticides
- Clean fuel-oriented investigation of thiophene oxidation by hydrogen peroxide using polyoxometalate as catalyst
- Aqueous foam stabilized by polyoxyethylene dodecyl ether
Articles in the same Issue
- Magnetic nano- and microparticles in biotechnology
- Application of gas chromatography-mass spectrometry in research of traditional Chinese medicine
- Copper determination using ICP-MS with hexapole collision cell
- Reactivation of a palladium catalyst during glucose oxidation by molecular oxygen
- Robust stabilization of a chemical reactor
- Influence of production progress on the heavy metal content in flax fibers
- In vitro antifungal and antibacterial properties of thiodiamine transition metal complexes
- Synthesis, characterization, and antimicrobial activity of new benzoylthiourea ligands
- Investigation of DNA cleavage activities of new oxime-type ligand complexes and molecular modeling of complex-DNA interactions
- Characterization of mechanochemically synthesized lead selenide
- Hydroxyapatite modified with silica used for sorption of copper(II)
- Corrosion resistance of zinc electrodeposited from acidic and alkaline electrolytes using pulse current
- Ternary composites of multi-wall carbon nanotubes, polyaniline, and noble-metal nanoparticles for potential applications in electrocatalysis
- Synthesis of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine derivatives
- Key side products due to reactivity of dimethylmaleoyl moiety as amine protective group
- Comparative DFT study on the α-glycosidic bond in reactive species of galactosyl diphosphates
- Gas chromatographic retention times prediction for components of petroleum condensate fraction
- Gas chromatography with surface ionization detection of nitro pesticides
- Clean fuel-oriented investigation of thiophene oxidation by hydrogen peroxide using polyoxometalate as catalyst
- Aqueous foam stabilized by polyoxyethylene dodecyl ether