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.

scholarly journals Dietary glutamic acid and aspartic acid as biomarkers for predicting diabetic retinopathy

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
So Young Park ◽  
Jieun Kim ◽  
Jung Il Son ◽  
Sang Youl Rhee ◽  
Do-Yeon Kim ◽  
...  
Keyword(s):  
Diabetic Retinopathy ◽  
Glutamic Acid ◽  
Aspartic Acid ◽  
Education Level ◽  
Screening Rate ◽  
Food Records ◽  
Acid Intake ◽  
Lower Education Level ◽  
Lower Education

AbstractThe screening rate of diabetic retinopathy (DR) is low despite the importance of early diagnosis. We investigated the predictive value of dietary glutamic acid and aspartic acid for diagnosis of DR using the Korea National Diabetes Program cohort study. The 2067 patients with type 2 diabetes without DR were included. The baseline intakes of energy, glutamic acid and aspartic acid were assessed using a 3-day food records. The risk of DR incidence based on intake of glutamic acid and aspartic acid was analyzed. The DR group was older, and had higher HbA1c, longer DM duration, lower education level and income than non-DR group (all p < 0.05). The intake of total energy, glutamic acid and aspartic acid were lower in DR group than non-DR group (p = 0.010, p = 0.025 and p = 0.042, respectively). There was no difference in the risk of developing DR according to the intake of glutamic acid and ascorbic acid. But, aspartic acid intake had a negative correlation with PDR. Hence, the intake of glutamic acid and aspartic acid did not affect in DR incidence. However, lower aspartic acid intake affected the PDR incidence.

scholarly journals Biodegradable poly(D,L-lactide-co-glycolide)/poly(L-γ-glutamic acid) nanoparticles conjugated to folic acid for targeted delivery of doxorubicin

2017 ◽  
Vol 76 ◽  
pp. 743-751 ◽  
Author(s):  
Laura Jaimes-Aguirre ◽  
Enrique Morales-Avila ◽  
Blanca E. Ocampo-García ◽  
Luis Alberto Medina ◽  
Gustavo López-Téllez ◽  
...  
Keyword(s):  
Folic Acid ◽  
Glutamic Acid ◽  
Targeted Delivery ◽  
Biodegradable Poly

Biodegradation of copoly(L-aspartic acid/L-glutamic acid) in vitro

Biopolymers ◽  
1990 ◽  
Vol 29 (3) ◽  
pp. 549-557 ◽  
Author(s):  
Toshio Hayashi ◽  
Makoto Iwatsuki
Keyword(s):  
Glutamic Acid ◽  
Aspartic Acid

scholarly journals Utilization in vivo of glucose and volatile fatty acids by sheep brain for the synthesis of acidic amino acids

1966 ◽  
Vol 101 (3) ◽  
pp. 591-597 ◽  
Author(s):  
R M O'Neal ◽  
R E Koeppe ◽  
E I Williams
Keyword(s):  
Amino Acids ◽  
Fatty Acids ◽  
Glutamic Acid ◽  
Aspartic Acid ◽  
Free Amino Acids ◽  
Free Amino ◽  
Specific Activity ◽  
Tricarboxylic Acid Cycle ◽  
Sheep Brain ◽  
The Brain

1. Free glutamic acid, aspartic acid, glutamic acid from glutamine and, in some instances, the glutamic acid from glutathione and the aspartic acid from N-acetyl-aspartic acid were isolated from the brains of sheep and assayed for radioactivity after intravenous injection of [2-(14)C]glucose, [1-(14)C]acetate, [1-(14)C]butyrate or [2-(14)C]propionate. These brain components were also isolated and analysed from rats that had been given [2-(14)C]propionate. The results indicate that, as in rat brain, glucose is by far the best precursor of the free amino acids of sheep brain. 2. Degradation of the glutamate of brain yielded labelling patterns consistent with the proposal that the major route of pyruvate metabolism in brain is via acetyl-CoA, and that the short-chain fatty acids enter the brain without prior metabolism by other tissue and are metabolized in brain via the tricarboxylic acid cycle. 3. When labelled glucose was used as a precursor, glutamate always had a higher specific activity than glutamine; when labelled fatty acids were used, the reverse was true. These findings add support and complexity to the concept of the metabolic; compartmentation' of the free amino acids of brain. 4. The results from experiments with labelled propionate strongly suggest that brain metabolizes propionate via succinate and that this metabolic route may be a limited but important source of dicarboxylic acids in the brain.

scholarly journals Modification process in nixtamalization of folic acid-rich dent corn (Zea mays identata) and its identification as smart food fortificant

2018 ◽  
Vol 154 ◽  
pp. 01017 ◽  
Author(s):  
Agustine Susilowati ◽  
Puspa Dewi Lotulung ◽  
Yati Maryati ◽  
Aspiyanto
Keyword(s):  
Zea Mays ◽  
Folic Acid ◽  
Glutamic Acid ◽  
Relative Intensity ◽  
Reducing Sugar ◽  
Total Sugar ◽  
Initial Material ◽  
Operation Condition ◽  
Modification Process ◽  
Dent Corn

A modification on nixtamalization process of dent corn (Zea mays identata) was conducted in order to recover natural folic acid-rich corn. Nixtamalization process on varieties of white dent corn and yellow dent corn subsequently were performed by steeping solution of Ca(OH)2 at concentrations of 0, 10, 20 and 30 % (w/w corn dissolved protein) for 18 hours, and boiling at 90 °C for 15, 30, 45 and 60 minutes. Result of research showed that concentration of Ca(OH)2 solution becoming more and more high and long boiling time increased both folic acid and reducing sugar, dropped total solids and total sugar, and fluctuated dissolved protein for both types of corn. Nixtamalization optimalization of white dent corn and yellow dent corn were achieved at combination of Ca(OH)2 20 % (w/w corn dissolved protein) for 60 minutes of boiling and Ca(OH)2 30 % for 30 minutes of boiling and gave folic acid of 466.81 and 506.74 μg/mL, respectively. In this condition, it is occurred an increase of folic acid 192.3 % (1.9 folds) and 139.89 % (1.4 folds) when compared to initial material of corn. Identification on folic acid monomer and glutamic acid monomer of both nixtamalized dent corn and yellow dent corn at optimum operation condition displayed domination of folic acid monomer with molecular weight (MW) 442.56 Dalton (Da.) with relative intensity 25.51 %, and 441.73 Da. with relative intensity 100 %, while glutamic acid monomer of nixtamalized yellow dent corn and nixtamalized white dent corn were dominated by monomer with MWs of 148.27 Da. and 148.32 Da., and relative intensity 3.73 and 1.8 %.

EXCRETION OF 4(5)-AMINO-5(4)-IMIDAZOLECARBOXAMIDE AND FORMIMINO-L-GLUTAMIC ACID IN FOLIC ACID AND VITAMIN B12 DEFICIENT RATS

1965 ◽  
Vol 43 (8) ◽  
pp. 1367-1374 ◽  
Author(s):  
P. L. McGeer ◽  
N. P. Sen ◽  
D. A. Grant
Keyword(s):  
Folic Acid ◽  
Glutamic Acid ◽  
Fold Increase ◽  
Urocanic Acid ◽  
Vitamin B ◽  
Deficient Diet ◽  
Intraperitoneal Dose ◽  
Group A ◽  
Acid Load ◽  
Deficient Group

The excretion of 4(5)-amino-5(4)-imidazolecarboxamide (AIC) in the urines of normal rats, rats raised on a folic acid deficient diet, and rats raised on a vitamin B12 deficient diet was measured. The AIC excretion was elevated 3-fold above normal in the B12 deficient group and 1.5-fold above normal in the folic acid deficient group.No evidence could be found that the raised AIC excretion was associated with a block in the conversion of AIC to purines. The recovery of radioactive AIC in the urine after an intraperitoneal dose of 2 μmoles AIC per kg was not increased over normal in any of the deficient groups, and was significantly less than normal in the B12-deficient group. Most of the urinary radioactivity in all groups was in allantoin, uric acid, and purines.When a load of 220 μmoles of AIC per kg was administered there was no difference between the vitamin B12 deficient and the normal groups in AIC recovery in the urine. When a load of 220 μmoles of urocanic acid per kg was administered, however, the B12-deficient group had an 18-fold increase over normal in Figlu excretion, and the folic acid deficient group a 17-fold increase. Thus, a substantial block in formimino-L-glutamic acid (Figlu) metabolism, but not in AIC metabolism, existed in the vitamin-deficient groups.Feeding a B12-deficient group a 2% methionine supplement reduced the Figlu excretion after a urocanic acid load to less than half that observed in B12-deficient groups without methionine supplementation, but had no influence on the AIC excretion.

Nanocomposites of hydroxyapatite with aspartic acid and glutamic acid and their interaction with osteoblast-like cells

Biomaterials ◽  
2006 ◽  
Vol 27 (25) ◽  
pp. 4428-4433 ◽  
Author(s):  
E BOANINI ◽  
P TORRICELLI ◽  
M GAZZANO ◽  
R GIARDINO ◽  
A BIGI
Keyword(s):  
Glutamic Acid ◽  
Aspartic Acid
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