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

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.

Automated summary

A new nitrogen-rich furan compound, 3-acetamido-5-acetyl furan (3A5AF), was discovered from chitin biomass. A reactive synthon, 3-acetamido-5-furfuryl aldehyde (3A5F), was developed and demonstrated to be a source of bio-derived nitrogen-rich heteroaromatics, carbocycles, and bioconjugation reagents.