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 access...

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Bibliographic Details
Published in:Applied biochemistry and biotechnology 2004, Vol.113-116 (1-3), p.857-869
Main Authors: Holladay, Johnathan E, Werpy, Todd A, Muzatko, Danielle S
Format: Article
Language:English
Subjects:
Amino acids
Biomass
Biorefineries
Biotechnology - methods
Carbon - chemistry
Catalysis
Catalytic converters
Chemical reactions
Chemistry, Organic - methods
Coupling (molecular)
Deamination
Decarboxylation
Desorption
Fermentation
Fossil fuels
Glutamic acid
Glutamic Acid - chemistry
Hydrogen - chemistry
Hydrogenation
Intermediates
Ionization
Ions
Magnetic Resonance Spectroscopy
Models, Chemical
Monomers
NMR
Nuclear fuels
Nuclear magnetic resonance
Peptides
Petrochemicals
Phosphoric Acids - chemistry
Pyrroles - chemistry
Pyrrolidines - chemistry
Pyrrolidonecarboxylic Acid - chemistry
Spectrophotometry
Studies
Time Factors
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Summary: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.
ISSN:0273-2289
0273-2289
1559-0291
DOI:10.1385/ABAB:115:1-3:0857