The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates

Scholarly Works

• Barranco, S.; Cuccu, F.; Uras, M.; Frongia, A. The Heyns Rearrangement: Synthetic Routes Beyond Carbohydrate Chemistry. Chemistry (Weinheim an der Bergstrasse, Germany) 2024, e202400355. doi:10.1002/chem.202400355
• Panda, S.; Ghorai, P. Expedient Access to Enantioenriched 1-Azaspiro Cyclobutanones Enabled by Modified Heyns Rearrangement. Angewandte Chemie (International ed. in English) 2023, 62, e202306179. doi:10.1002/anie.202306179
• Panda, S.; Ghorai, P. Expedient Access to Enantioenriched 1‐Azaspiro Cyclobutanones Enabled by Modified Heyns Rearrangement. Angewandte Chemie 2023, 135. doi:10.1002/ange.202306179
• Vasantharaju, S. G.; Murkute, S. R.; Singh, G. P.; Bhat, K.; Godbole, H. M.; Upadhyay, P. R.; Trivedi, A. Identification, Synthesis, Isolation, and Characterization of Formulation Related Degradation Impurity of Cefadroxil Oral Suspension. Elsevier BV 2023. doi:10.2139/ssrn.4606423
• Cao, J.; Su, Y.; Zhang, X.; Zhu, S. Highly Enantioselective Brønsted Acid Catalyzed Heyns Rearrangement. Angewandte Chemie 2022, 135. doi:10.1002/ange.202212976
• Cao, J.; Su, Y.-X.; Zhang, X.-Y.; Zhu, S.-F. Highly Enantioselective Brønsted Acid Catalyzed Heyns Rearrangement. Angewandte Chemie (International ed. in English) 2022, 62, e202212976. doi:10.1002/anie.202212976
• Choutka, J.; Kratochvíl, M.; Císařová, I.; Pohl, R.; Kaminský, J.; Parkan, K. Silicon-bridged (1→1)-disaccharides: an umpoled glycomimetic scaffold. Organic & biomolecular chemistry 2022, 20, 7613–7621. doi:10.1039/d2ob01161a
• Nie, X.-K.; Chen, Y.; Zhang, S.-Q.; Cui, X.; Tang, Z.; Li, G.-X. Chiral Primary Amine Catalyzed Enantioselective Tandem Reactions Based on Heyns Rearrangement: Synthesis of α-Tertiary Amino Ketones. Organic letters 2022, 24, 2069–2074. doi:10.1021/acs.orglett.2c00724
• Huang, J.; Chen, J.-F.; Cui, X.; Zhao, J.-Z.; Tang, Z.; Li, G.-X. Preparation of Dihydronaphthofurans from α-Hydroxyl Ketones via a One-Pot Multicomponent Reaction Based on Heyns Rearrangement. The Journal of organic chemistry 2022, 87, 3311–3318. doi:10.1021/acs.joc.1c02958
• Li, L.; Zhang, S.; Deng, X.; Li, G.; Tang, Z.; Zhao, G. Preparation and Application of α-Imino Ketones through One-Pot Tandem Reactions Based on Heyns Rearrangement. Organic letters 2021, 23, 6819–6824. doi:10.1021/acs.orglett.1c02390
• Schmutzler, S.; Knappe, D.; Marx, A.; Hoffmann, R. Solid-phase synthesis of D-fructose-derived Heyns peptides utilizing N α -Fmoc-Lysin[N ε -(2-deoxy-D-glucos-2-yl),N ε -Boc]-OH as building block. Amino acids 2021, 53, 881–891. doi:10.1007/s00726-021-02989-7
• Guo, L.; Chen, Z.; Zhu, H.; Li, M.; Gu, Y. Acid-catalyzed chemodivergent reactions of 2,2-dimethoxyacetaldehyde and anilines. Chinese Chemical Letters 2021, 32, 1419–1422. doi:10.1016/j.cclet.2020.10.033
• Raja, D.; Philips, A.; Palani, P.; Lin, W.-Y.; Devikala, S.; Senadi, G. C. Metal-Free Synthesis of Benzimidazoles via Oxidative Cyclization of d-Glucose with o-Phenylenediamines in Water. The Journal of organic chemistry 2020, 85, 11531–11540. doi:10.1021/acs.joc.0c01053
• Pommier, M.; Vidal, S. Anomeric Spiro-Annulated Glycopyranosides: An Overview of Synthetic Methodologies and Biological Applications. Topics in Heterocyclic Chemistry; Springer International Publishing, 2019; pp 1–25. doi:10.1007/7081_2019_33
• Köckinger, M.; Hone, C. A.; Kappe, C. O. HCN on Tap: On-Demand Continuous Production of Anhydrous HCN for Organic Synthesis. Organic letters 2019, 21, 5326–5330. doi:10.1021/acs.orglett.9b01941
• Prasch, H.; Hojnik, C.; Lindhorst, T. K.; Didak, B.; Landemarre, L.; Wrodnigg, T. M. New lectin ligands: Testing of Amadori rearrangement products with a series of mannoside-specific lectins. Carbohydrate research 2019, 475, 65–68. doi:10.1016/j.carres.2019.01.010
• Yang, Y.; Yu, B. Recent Advances in the Chemical Synthesis of C-Glycosides. Chemical reviews 2017, 117, 12281–12356. doi:10.1021/acs.chemrev.7b00234
• Roviello, G. N.; Iannitti, R.; Palumbo, R.; Simonyan, H. M.; Vicidomini, C.; Roviello, V. Lac-L-TTA, a novel lactose-based amino acid-sugar conjugate for anti-metastatic applications. Amino acids 2017, 49, 1347–1353. doi:10.1007/s00726-017-2433-2
• Villadsen, K.; Martos-Maldonado, M. C.; Jensen, K. J.; Thygesen, M. B. Chemoselective reactions for the synthesis of glycoconjugates from unprotected carbohydrates. Chembiochem : a European journal of chemical biology 2017, 18, 574–612. doi:10.1002/cbic.201600582
• Azad, C. S.; Saxena, M.; Siddiqui, A. J.; Bhardwaj, J.; Puri, S. K.; Dutta, G.; Anand, N.; Saxena, A. K. Synthesis of primaquine glyco-conjugates as potential tissue schizontocidal antimalarial agents. Chemical biology & drug design 2017, 90, 254–261. doi:10.1111/cbdd.12944

Explore citations to this article at