Unlocking the Potential of Bio-Based Nitrogen-Rich Furanic Platforms as Biomass Synthons.

Autor: Gomes RFA; Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003, Lisbon, Portugal.; Yusuf Hamied Department of Chemistry, University of Cambridge, CB2 1EW, Cambridge, UK., Gonçalves BMF; Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003, Lisbon, Portugal., Andrade KHS; Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003, Lisbon, Portugal., Sousa BB; Instituto de Medicina Molecular, João Lobo Antunes, Faculdade de Medicina da, Universidade de Lisboa, 1649-028, Lisboa, Portugal., Maulide N; Institute of Organic Chemistry, University of Vienna, 1090, Vienna, Austria., Bernardes GJL; Yusuf Hamied Department of Chemistry, University of Cambridge, CB2 1EW, Cambridge, UK.; Instituto de Medicina Molecular, João Lobo Antunes, Faculdade de Medicina da, Universidade de Lisboa, 1649-028, Lisboa, Portugal., Afonso CAM; Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003, Lisbon, Portugal.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2023 Jul 10; Vol. 62 (28), pp. e202304449. Date of Electronic Publication: 2023 Jun 01.
DOI: 10.1002/anie.202304449
Abstrakt: The demand for new biomass-derived fine and commodity chemicals propels the discovery of new methodologies and synthons. Whereas furfural and 5-hydroxymethylfurfural are cornerstones of sustainable chemistry, 3-acetamido-5-acetyl furan (3A5AF), an N-rich furan obtained from chitin biomass, remains unexplored, due to the poor reactivity of the acetyl group relative to previous furanic aldehydes. Here we developed a reactive 3-acetamido-5-furfuryl aldehyde (3A5F) and demonstrated the utility of this synthon as a source of bio-derived nitrogen-rich heteroaromatics, carbocycles, and as a bioconjugation reagent.
(© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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