Catalytic hydrogenation of glutamic acid.
Technology to convert biomass into chemical building blocks provides an opportunity to displace fossil fuels and increase the economic viability of biorefineries. Coupling fermentation capability with aqueous-phase catalysis provides novel routes to monomers and chemicals, including those not accessible from petrochemical routes. Glutamic acid provides a platform to numerous compounds through thermochemical approaches including hydrogenation, cyclization, decarboxylation, and deamination. Hydrogenation of amino acids also provides access to chiral compounds with high enantiopurity. This article details aqueous-phase hydrogenation reactions that we have developed that lead to valuable chemical intermediates from glutamic acid. In addition, 13C nuclear magnetic resonance and matrix- assisted laser desorption ionization mass spectral data are presented that provide a mechanistic picture of the reactions. The results show that hydrogenation of glutamic acid has unique characteristics from other amino acids and that paradigms in the literature do not hold up for this transformation.
Holladay
Johnathan E
JE
Pacific Northwest National Laboratory, PO Box 999, MSIN: K2-12, 902 Battelle Boulevard, Richland, WA 99352, USA. john.holladay@pnl.gov
Werpy
Todd A
TA
Muzatko
Danielle S
DS
D001709:Biotechnology / Q000379:methods*; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D005285:Fermentation; D018698:Glutamic Acid / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D010756:Phosphoric Acids / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry; D011761:Pyrrolidonecarboxylic Acid / Q000737:chemistry; D013053:Spectrophotometry; D013997:Time Factors
D010756:Phosphoric Acids; D011758:Pyrroles; D011759:Pyrrolidines; C431590:pyroglutaminol; D018698:Glutamic Acid; C010509:prolinol; D002244:Carbon; D006859:Hydrogen; C030242:phosphoric acid; D011761:Pyrrolidonecarboxylic Acid