1188-37-0

Basic information

• Product Name: N-Acetyl-L-glutamic acid
• Synonyms: acetylglutamicacid;L-Glutamic acid, N-acetyl-;l-glutamicaci;l-n-acetylglutamicacid;n-acetylglutamate;n-acetylglutamic;N-Acetylglutamic acid;n-acetyl-glutamicaci
• CAS NO: 1188-37-0
• Molecular Formula: C₇H₁₁NO₅
• Molecular Weight: 189.17
• EINECS: 214-708-4
• Product Categories: Amino Acid Derivatives;Glutamic acid [Glu, E];Ac-Amino Acids;Amino Acids;Amino Acids (N-Protected);Biochemistry;Amino Acid Derivatives;Glutamic Acid;Peptide Synthesis;amino acid;amino
• Mol File: 1188-37-0.mol
• Article Data: 14

Chemical Properties

• Melting Point: 194-196 °C(lit.)
• Boiling Point: 324.41°C (rough estimate)
• Flash Point: 253.7 ºC
• Appearance: white crystalline powder
• Density: 1.4119 (rough estimate)
• Vapor Pressure: 3.48E-11mmHg at 25°C
• Refractive Index: -15 ° (C=1, H2O)
• Storage Temp.: 0-6°C
• Solubility: 36g/l (Lit.)
• PKA: 3.45±0.10(Predicted)
• Water Solubility: 2.7 g/100 mL (20 ºC)
• BRN: 1727473
• CAS DataBase Reference: N-Acetyl-L-glutamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl-L-glutamic acid(1188-37-0)
• EPA Substance Registry System: N-Acetyl-L-glutamic acid(1188-37-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 2
• RTECS: LZ9725000
• TSCA: Yes
• Hazardous Substances Data: 1188-37-0(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

Different sources of media describe the Uses of 1188-37-0 differently. You can refer to the following data:
1. N-Acetyl-L-glutamic Acid is the N-Acetyl analogue of the non-essential amino acid, L-glutamic acid (G596960). N-Acetyl-L-glutamic Acid activates carbamoyl phosphate synthetase in the urea cycle.
2. Substrate for acetylglutamate kinase. Inhibitor of N-acetyl-L-glutamate synthetase
3. N-Acetyl-L-glutamic acid is used as pharmaceutical intermediates.

Purification Methods

A likely impurity is glutamic acid. Crystallise it from boiling water. It inhibits N-acetyl-L-glutamate synthase. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 p 1948 1961, Shigesada & Tatibana Eur J Biochem 84 285 1978, Coude Biochem Biophys Res Commun 102 1016 1981, Beilstein 4 IV 3047.]

InChI:InChI=1/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)/p-2/t5-/m0/s1

Synthetic route

L-glutamic acid (56-86-0) + acetic anhydride (108-24-7) → N-acetyl-(S)-glutamic acid

Conditions	Yield
In water for 0.0666667h; Irradiation;	98%
at 0 - 20℃;	61%
With water	58%
With acetic acid Heating;

+ L-glutamic acid (56-86-0) + 1-methyl-4-nitrosobenzene (623-11-0) → Acetyl-D,L-glutaminsaeure (5817-08-3) + N-acetyl-(S)-glutamic acid (1188-37-0)

Ketene (463-51-4) + L-glutamic acid (56-86-0) → N-acetyl-(S)-glutamic acid (1188-37-0)

Conditions	Yield
With sodium hydroxide

N-Acetyl-L-2-aminopentanoic acid (15891-50-6) → N-acetyl-(S)-glutamic acid (1188-37-0)

Conditions	Yield
With hydrogen peroxide; trifluoroacetic acid In water-d2 Kinetics; Photolysis;

L-glutamic acid (56-86-0) + 2-acetyloxy-5-nitrobenzoic acid (17336-14-0) → N-acetyl-(S)-glutamic acid (1188-37-0)

Conditions	Yield
In water at 25℃; Kinetics; Concentration;

L-glutamic acid (56-86-0) + 2-acetoxy-5-chloro-benzoic acid (1734-62-9) → N-acetyl-(S)-glutamic acid (1188-37-0)

Conditions	Yield
In water at 25℃; Kinetics; Concentration;

L-glutamic acid (56-86-0) + aspirin (50-78-2) → N-acetyl-(S)-glutamic acid (1188-37-0)

Conditions	Yield
In water at 25℃; Kinetics; Concentration;

L-glutamic acid (56-86-0) + acetylcoenzyme A (72-89-9) → N-acetyl-(S)-glutamic acid (1188-37-0)

Conditions	Yield
With amino-acid N-acetyltransferase; sodium hydroxide In aq. buffer at 30℃; pH=8; Enzymatic reaction;

ethanol (64-17-5) + N-acetyl-(S)-glutamic acid (1188-37-0) → diethyl N-acetyl L-glutamic ester (1446-19-1)

Conditions	Yield
With carbon tetrabromide for 32h; Heating;	91%

methanol (67-56-1) + N-acetyl-(S)-glutamic acid (1188-37-0) → dimethyl (2S)-2-(acetylamino)pentane-1,5-dioate (2361-99-1)

Conditions	Yield
With carbon tetrabromide for 20h; Heating;	88%
With thionyl chloride at 0℃; for 4h;	84%

N-acetyl-(S)-glutamic acid (1188-37-0) + isopropyl alcohol (67-63-0) → diisopropyl N-acetyl L-glutamic ester

Conditions	Yield
With carbon tetrabromide for 47h; Heating;	87%

N-acetyl-(S)-glutamic acid (1188-37-0) + glycerol (56-81-5) → rac-1-O-(Nα-acetyl-L-glutam-1-yl)glycerol (388587-60-8) + rac-2-O-(Nα-Ac-L-glutam-1-yl)glycerol

Conditions	Yield
With DL-dithiothreitol; papain In various solvent(s) at 50℃; for 24h;	A 53% B n/a

N-acetyl-(S)-glutamic acid (1188-37-0) + zopiclon (43200-80-2) → (R)-zopiclone N-acetyl-L-glutamate (1107971-21-0)

Conditions	Yield
In acetone at 35 - 37℃; for 1h; Heating / reflux;	48%
In acetone at 35 - 37℃; for 1h; Heating / reflux;	48%

N-acetyl-(S)-glutamic acid (1188-37-0) + 1-chloromethoxy-3,3-dimethyl-triaz-1-ene 2-oxide (858135-02-1) → N-Ac DMA/NO-Glu-NO/DMA

Conditions	Yield
With sodium carbonate In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃;	43%

({3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl)(methyl)amine (148870-56-8) + N-acetyl-(S)-glutamic acid (1188-37-0) → (1S)-4,5-dimethoxy-1-[(methylamino)methyl]benzocyclobutane N-acetyl-L-glutamic acid

Conditions	Yield
In ethanol for 1h; Reflux;	43%

N-acetyl-(S)-glutamic acid (1188-37-0) + (±)-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methylamine (73344-75-9) → (1S)-4,5-dimethoxy-1-(aminomethyl)-benzocyclobutane N-acetyl-L-glutamate (869856-08-6)

Conditions	Yield
In ethanol; water at 20℃; Heating / reflux; Industry scale;	40%

N-acetyl-(S)-glutamic acid (1188-37-0) + C15H15ClO3 → N-Ac NAP-Glu-NAP

Conditions	Yield
With sodium carbonate; potassium iodide In dimethylformamide [DMF] at 20℃;	30%

N-acetyl-(S)-glutamic acid (1188-37-0) + (±)-2-phenyl-1-[2-(piperidin-1-yl)phenyl]ethylamine (107362-46-9) → (S,S)-2-phenyl-1-[2-(piperidin-1-yl)phenyl]ethylamine-N-acetyl-L-glutamate salt

Conditions	Yield
In methanol; acetone Reflux;	25.5%

diazomethane (186581-53-3, 908094-01-9) + N-acetyl-(S)-glutamic acid (1188-37-0) → dimethyl (2S)-2-(acetylamino)pentane-1,5-dioate (2361-99-1)

Conditions	Yield
With 1,4-dioxane; diethyl ether
In diethyl ether

N-acetyl-(S)-glutamic acid (1188-37-0) → N2-acetyl-N5-phenyl-DL-glutamine (5817-10-7)

Conditions	Yield
With acetic anhydride Erhitzen des Reaktionsprodukts mit Anilin;

Upstream product

• 56-86-0 L-glutamic acid 
• 72-89-9 acetylcoenzyme A 
• 50-78-2 aspirin 
• 1734-62-9 2-acetoxy-5-chloro-benzoic acid 
• 17336-14-0 2-carboxy-4-nitrophenyl acetate 
• 463-51-4 Ketene 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 15891-50-6 N-Acetyl-L-2-aminopentanoic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 5817-10-7 N²-acetyl-N⁵-phenyl-DL-glutamine 
• 149-87-1 Pyroglutamic acid 
• 1334394-70-5 C₁₆H₁₆Cl₂N₆O₄ 
• 2361-99-1 N-Acetyl-L-glutaminsaeure-dimethylester 
• 1446-19-1 diethyl N-acetyl L-glutamic ester 

Relevant articles and documents

Deciphering Carbamoylpolyoxamic Acid Biosynthesis Reveals Unusual Acetylation Cycle Associated with Tandem Reduction and Sequential Hydroxylation

Polyoxin, produced by Streptomcyes cacaoi var. asoensis and Streptomyces aureochromogenes, contains two non-proteinogenic amino acids, carbamoylpolyoxamic acid (CPOAA) and polyoximic acid. Although the CPOAA moiety is highly unusual, its biosynthetic logic has remained enigmatic for decades. Here, we address CPOAA biosynthesis by reconstitution of its pathway. We demonstrated that its biosynthesis is initiated by a versatile N-acetyltransferase, PolN, catalyzing L-glutamate (1) to N-acetyl glutamate (2). Remarkably, we verified that PolM, a previously annotated dehydrogenase, catalyzes an unprecedented tandem reduction of acyl-phosphate to aldehyde, and subsequently to alcohol. We also unveiled a distinctive acetylation cycle catalyzed by PolN to synthesize α-amino-δ-hydroxyvaleric acid (6). Finally, we report that PolL is capable of converting a rare sequential hydroxylation of α-amino-δ-carbamoylhydroxyvaleric acid (7) to CPOAA. PolL represents an intriguing family of Fe(II)-dependent α-ketoglutarate dioxygenase with a cupin fold. These data illustrate several novel enzymatic reactions, and also set a foundation for rational pathway engineering for polyoxin production.

New method of synthesis of D,L-5-oxoproline

A new method for synthesis of D,L-5-oxoproline from N-acetyl-L-glutamic acid in weakly acid medium in the presence of water, and hydrolysis of an acetyl group and cyclization and total racemization of the acid simultaneously take place.The advantage of the method is the possibility of obtaining two individual amino acids with high yields in one chemical process using L-glutamic acid.

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