Catalytic Hydrogenation of Glutamic Acid

2004 ◽  
pp. 857-869
Author(s):  
Johnathan E. Holladay ◽  
Todd A. Werpy ◽  
Danielle S. Muzatko
Keyword(s):  
Glutamic Acid ◽  
Catalytic Hydrogenation

scholarly journals Synthesis of L-2-(N-Pteroylamino )-3-(N -phosphonoacetyl)aminopropanoic Acid as an Analogue of the Putative Phosphorylated Intermediate in the γ-Glutamation of Folic Acid by Folylpolyglutamate Synthetase

Pteridines ◽  
1999 ◽  
Vol 10 (1) ◽  
pp. 39-46 ◽  
Author(s):  
Ronald Forsch ◽  
Henry Bader ◽  
Andre Rosowsky
Keyword(s):  
Folic Acid ◽  
Glutamic Acid ◽  
Aspartic Acid ◽  
Catalytic Hydrogenation ◽  
Spatial Orientation ◽  
Sequential Treatment ◽  
Folylpolyglutamate Synthetase ◽  
Phosphonate Esters ◽  
Catalytic Addition

L-2-(N-Pteroyl)amino-3-(N-phosphonoacetyl)aminopropanoic acid was synthesized as an analogue of the putative y-phosphorylated intermediate in the enzyme-catalyzed γ-glutamation of folic acid by folylpolyglutamate synthetase (FPGS). N-(Benzyloxycarbonyl)-L-aspartic acid was converted in four steps to methyl L-2-(N-benzyloxycarbonyl)amino-3-aminopropanoate, and the latter was allowed to react with p-nitrophenyl dimethoxyphosphonoacetate to obtain methyl L-2-(N-benzyloxycarbonylamino)- 3-(N-dimethoxyphosphonoacetyl)aminopropanoate. After catalytic hydrogenation, the resulting amine was coupled to N10-formylpteroic acid via the mixed carboxylic-carbonic anhydride method, and the three ester groups were removed by sequential treatment with Me3SiBr in DMF and NaOH in DMSO. When the last step was performed only with NaOH/DMSO, one of the phosphonate esters remained intact, giving L-2-(N -pteroyl )amino-3 -(N -monOInethoxyphosphonoacetyl )aminopropanoic acid. Also synthesized as a potential FPGS inhibitor was Nα-(4-amino-4-deoxy-N10-methylpteroyl)-Nε-phosphonoacetyl- L-Iysine. The ability of these phosphonoacetyl derivatives to inhibit catalytic addition of L-glutamic acid to folic acid proved to be very low, suggesting that replacement of the CH2C(=O)OP(=O)(OH)2 moiety by NHC(=O)CH2P(=O)(OH)2 may place the terminal phosphonyl group in an unfavorable spatial orientation for binding to the enzyme.

Catalytic Hydrogenation of Glutamic Acid

2004 ◽  
Vol 115 (1-3) ◽  
pp. 0857-0870 ◽  
Author(s):  
Johnathan E. Holladay ◽  
Todd A. Werpy ◽  
Danielle S. Muzatko
Keyword(s):  
Glutamic Acid ◽  
Catalytic Hydrogenation

Autoantibodies in IDDM primarily recognize the 65,000-M(r) rather than the 67,000-M(r) isoform of glutamic acid decarboxylase

Diabetes ◽  
1993 ◽  
Vol 42 (4) ◽  
pp. 631-636 ◽  
Author(s):  
W. A. Hagopian ◽  
B. Michelsen ◽  
A. E. Karlsen ◽  
F. Larsen ◽  
A. Moody ◽  
...  
Keyword(s):  
Glutamic Acid ◽  
Glutamic Acid Decarboxylase ◽  
Acid Decarboxylase

Nanometer Scale Spectroscopic Visualization of Catalytic Sites During a Hydrogenation Reaction on a Pd/Au Bimetallic Catalyst

2020 ◽  
Author(s):  
hao yin ◽  
Liqing Zheng ◽  
Wei Fang ◽  
Yin-Hung Lai ◽  
Nikolaus Porenta ◽  
...  
Keyword(s):  
Catalytic Hydrogenation ◽  
Density Functional ◽  
Hydrogen Transfer ◽  
Bimetallic Catalyst ◽  
Local Environment ◽  
Hydrogenation Reaction ◽  
Boundary Density ◽  
Catalytic Sites ◽  
Powerful Analytical Tool ◽  
Tip Enhanced Raman Spectroscopy

<p>Understanding the mechanism of catalytic hydrogenation at the local environment requires chemical and topographic information involving catalytic sites, active hydrogen species and their spatial distribution. Here, tip-enhanced Raman spectroscopy (TERS) was employed to study the catalytic hydrogenation of chloro-nitrobenzenethiol on a well-defined Pd(sub-monolayer)/Au(111) bimetallic catalyst (<i>p</i><sub>H2</sub>=1.5 bar, 298 K), where the surface topography and chemical fingerprint information were simultaneously mapped with nanoscale resolution (≈10 nm). TERS imaging of the surface after catalytic hydrogenation confirms that the reaction occurs beyond the location of Pd sites. The results demonstrate that hydrogen spillover accelerates hydrogenation at the Au sites within 20 nm from the bimetallic Pd/Au boundary. Density functional theory was used to elucidate the thermodynamics of interfacial hydrogen transfer. We demonstrate that TERS as a powerful analytical tool provides a unique approach to spatially investigate the local structure-reactivity relationship in catalysis.</p>

Nanometer Scale Spectroscopic Visualization of Catalytic Sites During a Hydrogenation Reaction on a Pd/Au Bimetallic Catalyst

2020 ◽  
Author(s):  
Hao Yin ◽  
Liqing Zheng ◽  
Wei Fang ◽  
Yin-Hung Lai ◽  
Nikolaus Porenta ◽  
...  
Keyword(s):  
Catalytic Hydrogenation ◽  
Density Functional ◽  
Hydrogen Transfer ◽  
Bimetallic Catalyst ◽  
Local Environment ◽  
Hydrogenation Reaction ◽  
Boundary Density ◽  
Catalytic Sites ◽  
Powerful Analytical Tool ◽  
Tip Enhanced Raman Spectroscopy

<p>Understanding the mechanism of catalytic hydrogenation at the local environment requires chemical and topographic information involving catalytic sites, active hydrogen species and their spatial distribution. Here, tip-enhanced Raman spectroscopy (TERS) was employed to study the catalytic hydrogenation of chloro-nitrobenzenethiol on a well-defined Pd(sub-monolayer)/Au(111) bimetallic catalyst (<i>p</i><sub>H2</sub>=1.5 bar, 298 K), where the surface topography and chemical fingerprint information were simultaneously mapped with nanoscale resolution (≈10 nm). TERS imaging of the surface after catalytic hydrogenation confirms that the reaction occurs beyond the location of Pd sites. The results demonstrate that hydrogen spillover accelerates hydrogenation at the Au sites within 20 nm from the bimetallic Pd/Au boundary. Density functional theory was used to elucidate the thermodynamics of interfacial hydrogen transfer. We demonstrate that TERS as a powerful analytical tool provides a unique approach to spatially investigate the local structure-reactivity relationship in catalysis.</p>

Novel Co-fermentation of Dendropanax morbifera Extract to Produce γ-aminobutyric Acid and Poly-γ-glutamic Acid

2019 ◽  
Vol 25 (6) ◽  
pp. 785-791
Author(s):  
Woong-Kyu Yoon ◽  
Jae-Won Choi ◽  
Jong-Soon Lim ◽  
Coralia V. Garcia ◽  
Sam-Pin Lee
Keyword(s):  
Glutamic Acid ◽  
Aminobutyric Acid ◽  
Dendropanax Morbifera
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