title: Development of a clickable designer monolignol for interrogation of lignification in plant cell walls.
abstract: Lignin is an abundant and essential polymer in land plants. It is a prime factor in the recalcitrance of lignocellulosic biomass to agricultural and industrial end-uses such as forage, pulp and papermaking, and biofuels. To better understand lignification at the molecular level, we are developing a lignin spectroscopic and imaging toolbox on one "negligible" auxiliary. Toward that end, we describe the design, synthesis, and characterization of a new designer monolignol, 3-O-propargylcaffeyl alcohol, which contains a bioorthogonal alkynyl functional group at the 3-O-position. Importantly, our data indicate that this monolignol does not alter the fidelity of lignification. We demonstrate that the designer monolignol provides a platform for multiple spectroscopic and imaging approaches to reveal temporal and spatial details of lignification, the knowledge of which is critical to reap the potential of energy-rich renewable plant biomass for sustainable liquid fuels and other diverse economic applications.
authors.affiliation: Department of Chemistry, Altoona College, The Pennsylvania State University , Altoona, Pennsylvania 16601, United States.
authors.forename: Natalie
authors.initials: N
authors.lastname: Bukowski
authors.forename: Jyotsna L
authors.initials: JL
authors.lastname: Pandey
authors.forename: Lucas
authors.initials: L
authors.lastname: Doyle
authors.forename: Tom L
authors.initials: TL
authors.lastname: Richard
authors.forename: Charles T
authors.initials: CT
authors.lastname: Anderson
authors.forename: Yimin
authors.initials: Y
authors.lastname: Zhu
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D017360:Arabidopsis / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D006735:Horseradish Peroxidase / Q000737:chemistry; D008031:Lignin / Q000032:analysis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015335:Molecular Probes / Q000138:chemical synthesis / Q000737:chemistry*; D059828:Plant Cells / Q000737:chemistry*; D018547:Plant Stems / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D036226:Seedlings / Q000737:chemistry; D013059:Spectrum Analysis, Raman
chemical_list: C000607321:3-O-propargylcaffeyl alcohol; D000480:Alkynes; D015335:Molecular Probes; D020005:Propanols; D008031:Lignin; D006735:Horseradish Peroxidase