5959-95-5

Basic information

• Product Name: D-Glutamine
• Synonyms: D(-)-GLUTAMIC ACID-5-AMIDE;D-GLUTAMIC ACID 5-AMIDE;D-GLUTAMINIC ACID 5-AMIDE;D(-)-GLUTAMINE;D-GLUTAMINE;D-2-AMINOGLUTARAMIC ACID;H-D-GLN-OH;(R)-2-AMINO-4-CARBAMOYL-BUTYRIC ACID
• CAS NO: 5959-95-5
• Molecular Formula: C₅H₁₀N₂O₃
• Molecular Weight: 146.14
• EINECS: 2017-001-1
• Product Categories: Amino ACIDS SERIES;pharmacetical;chiral;Glutamine [Gln, Q];Amino Acids and Derivatives;alpha-Amino Acids;Amino Acids;Biochemistry;Amino Acids and Derivatives;amino acid;Inhibitors
• Mol File: 5959-95-5.mol
• Article Data: 16

Chemical Properties

• Melting Point: 184-185 °C
• Boiling Point: 265.74°C (rough estimate)
• Flash Point: 223.3 °C
• Appearance: White/Powder
• Density: 1.3394 (rough estimate)
• Refractive Index: -33 ° (C=5, 5mol/L HCl)
• Storage Temp.: -15°C
• Solubility: Water (Slightly, Sonicated)
• PKA: 2.27±0.10(Predicted)
• Water Solubility: 42.53g/L(temperature not stated)
• BRN: 1723796
• CAS DataBase Reference: D-Glutamine(CAS DataBase Reference)
• NIST Chemistry Reference: D-Glutamine(5959-95-5)
• EPA Substance Registry System: D-Glutamine(5959-95-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 36/37/39-26-27-24/25
• WGK Germany: 3
• Hazardous Substances Data: 5959-95-5(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

Different sources of media describe the Uses of 5959-95-5 differently. You can refer to the following data:
1. D-Glutamine is an unnatural isomer of L-Glutamine (G597000) that is present in human plasma an is a source of liberated ammonia. D-Glutamine can be synthesized by enzymatic means or can be found in cheeses, wine and vinegars as well. It is often used to determine the activity of Glutamine synthetase, an enzyme that is commonly found in the mammalian liver and brain that controls the use of nitrogen in cells.
2. D-Glutamine has been used to study its role in conferring protection against acetaldehyde-induced disruption of barrier function in Caco-2 cell monolayer.

Definition

ChEBI: The D-enantiomer of glutamine.

General Description

Glutamine is a non-essential and the most abundant free amino acid present in the human body. It is an important component of proteins and is one of the 20 proteinogenic amino acids. It forms 5-6% of bound amino acids.

Biochem/physiol Actions

Glutamine forms the central metabolite in amino acid transamination via a-ketoglutarate and glutamic acid. This amino acid is metabolized by different enzymes, such as glutaminase, present in liver, and glutamine synthetase, present in skeletal muscle. It is produced in the cytoplasm from other amino acids, predominantly from branched-chain amino acids and glutamate. It plays an essential role in ammonia metabolism and detoxification. Its skeletal muscle levels are significantly reduced post trauma, operation and inflammatory states. It servers as a prognostic marker in fatal sepsis during which its skeletal muscle levels are decreased by 90%.

InChI:InChI=1/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m1/s1

Synthetic route

D-glutamic acid-5-hydrazide (19427-23-7) → D-Glutamin (5959-95-5)

Conditions	Yield
With ethanol; nickel

N2-(toluene-4-sulfonyl)-D-glutamine (42749-49-5) → D-Glutamin (5959-95-5)

Conditions	Yield
With ammonia; sodium

DL-5-carbamylethylhydantoin (69489-32-3) → D-Glutamin (5959-95-5)

Conditions	Yield
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h;
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h; pH 8.0; enzymatic reaction;

GLUTAMINE (56-85-9, 585-21-7, 5959-95-5, 6899-04-3) → D-Glutamin (5959-95-5) + L-glutamine (56-85-9)

Conditions	Yield
With (2R,3R,11R,12R)-(+)-18-crown-6-2,3,11,12-tetracarbonic acid
With R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6 coated C18 silica gel column at 25℃; pH=2; Resolution of racemate;

GLUTAMINE (56-85-9, 585-21-7, 5959-95-5, 6899-04-3) + benzeneacetic acid methyl ester (101-41-7) → D-Glutamin (5959-95-5) + α-N-phenylacetyl-L-glutamine (28047-15-6)

Conditions	Yield
With sodium hydroxide; E. coli penicillin-G acylase F24A mutant at 25℃; pH=9.0;

D-Glutamic acid (6893-26-1) → D-Glutamin (5959-95-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: HCl 2: H2O; N2H4+H2O 3: Raney nickel; aqueous ethanol View Scheme

(R)-2-amino-5-methoxy-5-oxopentanoic acid (6461-04-7) → D-Glutamin (5959-95-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O; N2H4+H2O 2: Raney nickel; aqueous ethanol View Scheme

5-oxo-1-(toluene-4-sulfonyl)-D-proline (882861-84-9) → D-Glutamin (5959-95-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; NH3 2: sodium; liquid NH3 View Scheme

1-(4'-methylbenzenesulfonyl)-5-oxopyrrolidine-2-carboxylic acid (21957-65-3) → D-Glutamin (5959-95-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: brucine 2: water; NH3 3: sodium; liquid NH3 View Scheme

(PPh3)2 PdCl2 + 1-acetamido-3-carbamoylpropene + 2-(2-isopropyl-5-methylcyclohexyloxy)ethanol → D-Glutamin (5959-95-5)

Conditions	Yield
With CO In tetrahydrofuran; hydrogenchloride

1-acetamido-3-carbamoylpropene + 2-(2-isopropyl-5-methylcyclohexyloxy)ethanol → D-Glutamin (5959-95-5)

Conditions	Yield
With CO; (PPh3)2PdCl2 In tetrahydrofuran; hydrogenchloride

jagaricin (1422729-34-7) → D-allo-threonine (24830-94-2) + (2S,3S)-2-amino-3-hydroxybutanoic acid (28954-12-3) + L-threonine (72-19-5) + D-Glutamin (5959-95-5) + (R)-3-hydroxytetradecanoic acid (28715-21-1) + dehydrobutyrine (20748-08-7) + tyrosine (556-02-5) + glycine (56-40-6) + L-histidine (71-00-1)

Conditions	Yield
With hydrogenchloride; phenol In water at 105℃; Reagent/catalyst;

...Expand

GLUTAMINE (56-85-9, 585-21-7, 5959-95-5, 6899-04-3) → D-Glutamin (5959-95-5)

Conditions	Yield
With fatty acid photodecarboxylase from Chlorella variabilis NC64A/G462Y mutant In aq. phosphate buffer; dimethyl sulfoxide at 20℃; for 12h; pH=8.5; Catalytic behavior; Reagent/catalyst; Irradiation; Resolution of racemate; Enzymatic reaction; enantioselective reaction;	n/a

D-Glutamin (5959-95-5) + (R)-N-(2-benzoyl-4-chlorophenyl)-2-[3,5-dihydro-4H-dinaphtho[2,1-c:1',2'-e]azepine-4-yl]acetamide + nickel(II) acetate tetrahydrate (6018-89-9) → C42H33ClN4NiO4

Conditions	Yield
With potassium carbonate In methanol at 60 - 70℃; for 3h; diastereoselective reaction;	93%

D-Glutamin (5959-95-5) + 3-carbamoyl-1-(2,4-dinitrophenyl)pyridinium chloride (53406-00-1) → C11H14N3O4(1+)

Conditions	Yield
With triethylamine In methanol at 20℃; for 48h;	88.2%

D-Glutamin (5959-95-5) + di-tert-butyl dicarbonate (24424-99-5) → (2R)-5-amino-2-(tert-butoxycarbonylamino)-5-oxo-pentanoic acid (61348-28-5)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 0℃; for 1h;	86%

D-Glutamin (5959-95-5) + benzyl bromide (100-39-0) → (R)-(+)-N,N-dibenzylglutamine benzyl ester

Conditions	Yield
With potassium carbonate In water at 20℃; for 240h; benzylation;	46%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.833333h;

D-Glutamin (5959-95-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2C5H6NO3(1-)*2Ba(2+)*CHO2(1-)*NO3(1-)

Conditions	Yield
With barium(II) nitrate In water at 100℃; for 72h;	0.78%

(R)-2-bromopropionyl chloride (7148-74-5, 22592-73-0, 71425-59-7, 52152-04-2) + D-Glutamin (5959-95-5) → N2-(2-bromo-propionyl)-glutamine

Conditions	Yield
With alkali ;

(R)-2-Bromo-4-methyl-pentanoyl chloride (28659-88-3, 59960-79-1, 104420-63-5) + D-Glutamin (5959-95-5) → N2-(2-bromo-4-methyl-valeryl)-glutamine

Conditions	Yield
With alkali ;

D-Glutamin (5959-95-5) + chloroacetyl chloride (79-04-9) → N2-chloroacetyl-glutamine (13139-62-3)

Conditions	Yield
With sodium hydroxide; diethyl ether chloroacetyl-d-glutamine;

D-Glutamin (5959-95-5) + phenylacetyl chloride (103-80-0) → α-N-phenylacetyl-L-glutamine (28047-15-6)

Conditions	Yield
With sodium hydrogencarbonate

D-Glutamin (5959-95-5) + telocinobufagin 3-hemisuberate p-nitrophenyl ester (75090-28-7) → telocinobufagin 3-suberoyl-D-glutamine ester (75104-51-7)

Conditions	Yield
In pyridine; water for 5h; Ambient temperature;	2 mg

D-Glutamin (5959-95-5) + marinobufagin 3-hemisuberate p-nitrophenyl ester (71156-90-6) → marinobufagin 3-suberoyl-D-glutamine ester (71156-91-7)

Conditions	Yield
In pyridine; water for 1h; Ambient temperature;	10 mg

D-Glutamin (5959-95-5) + (N-benzyloxycarbonyl)-L-alanine N-hydroxysuccinimide ester (3401-36-3) → Cbz-L-Ala-D-Gln (74842-54-9)

Conditions	Yield
With triethylamine; 1-amino-3-(dimethylamino)propane 1.) THF, H2O, 4 deg C, 24 h, 2.) THF, H2O, 1 h; Yield given. Multistep reaction;

D-Glutamin (5959-95-5) + γ-OSu-N-Z-L-Glu-OBzl (34897-67-1) → benzyloxycarbonyl-α-benzyl-γ-L-glutamyl-D-glutamine

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide for 24h; Ambient temperature; Yield given;

D-Glutamin (5959-95-5) + Oγ-benzyl-Nα-benzyloxycarbonylglutamic acid succinimidyl ester (67413-34-7) → benzyloxycarbonyl-γ-benzyl-α-L-glutamyl-D-glutamine (75898-60-1)

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide for 24h; Ambient temperature; Yield given;

D-Glutamin (5959-95-5) → γ-D-glutamyl-D-glutamine

Conditions	Yield
With Tris buffer (pH: 8.8) at 37℃; for 2h; transamidase from Bacillus natto; Yield given;
With γ-glutamyltransferase from Bacillus subtilis In aq. buffer at 22℃; for 24h; pH=8.5; pH-value; Enzymatic reaction;

D-Glutamin (5959-95-5) + dl-α-bromo-isocaproic acid chloride → N2-(2-bromo-4-methyl-valeryl)-glutamine

Conditions	Yield
With alkali ;

D-Glutamin (5959-95-5) + l-α-bromo-propionyl chloride → N2-(2-bromo-propionyl)-glutamine

Conditions	Yield
With alkali ;

α-ketoglutaric acid (328-50-7) + D-Glutamin (5959-95-5) → N2-(1-carboxyethyl)-D-glutamine

Conditions	Yield
With sodium cyanoborohydride; acetic acid In water pH=6.0 - 6.8;

D-Glutamin (5959-95-5) + carbonic acid 2,5-dioxopyrrolidin-1-yl ester 4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)benzyl ester (556050-48-7) → (R)-4-Carbamoyl-2-[4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl)-benzyloxycarbonylamino]-butyric acid

Conditions	Yield
With triethylamine In tetrahydrofuran; water at 25℃;

undec-10-enoyl chloride (38460-95-6) + D-Glutamin (5959-95-5) → (R)-4-Carbamoyl-2-undec-10-enoylamino-butyric acid

Conditions	Yield
With sodium carbonate In tetrahydrofuran at 20℃;

quinolin-2-ylmethylbromide (5632-15-5) + D-Glutamin (5959-95-5) → C25H24N4O3

Conditions	Yield
With sodium hydroxide In ethanol; water

D-Glutamin (5959-95-5) → (R)-4-Carbamoyl-2-undecanoylamino-butyric acid

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. Na2CO3 / tetrahydrofuran / 20 °C 2: H2 / Pd/C / methanol / 20 °C / atmospheric pressure View Scheme

D-Glutamin (5959-95-5) → (R)-2-((S)-2-Amino-propionylamino)-4-carbamoyl-butyric acid ethyl ester

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) Et3N, 2.) dimethylaminopropylamine / 1.) THF, H2O, 4 deg C, 24 h, 2.) THF, H2O, 1 h 2: 1.) aq. Cs2CO3 / 1.) THF, 2.) DMF, RT, 48 h 3: H2, HOAc, 1 N HCl / 5percent Pd/C / 2 h / 760 Torr View Scheme

Upstream product

• 27372-38-9 6-oxo-1,4,5,6-tetrahydropyridazine-3-carboxylic acid 
• 56-85-9 L-glutamine 
• 7664-41-7 ammonia 
• 98-79-3 L-Pyroglutamic acid 
• 7732-18-5 water 
• 56-85-9 GLUTAMINE 
• 1422729-34-7 jagaricin 
• 21957-65-3 1-(4'-methylbenzenesulfonyl)-5-oxopyrrolidine-2-carboxylic acid 
• 882861-84-9 5-oxo-1-(toluene-4-sulfonyl)-D-proline 
• 6461-04-7 (R)-2-amino-5-methoxy-5-oxopentanoic acid 
• 6893-26-1 D-Glutamic acid 
• 101-41-7 benzeneacetic acid methyl ester 
• 69489-32-3 DL-5-carbamylethylhydantoin 
• 42749-49-5 N²-(toluene-4-sulfonyl)-D-glutamine 

Downstream Products

• 2419-34-3 4-Carbamoyl-2-(2,2,2-trifluoro-acetylamino)-butyric acid 
• 85313-46-8 t-Bumeoc-Gln 
• 40217-11-6 4-amino-5-hydroxypentanoic acid 
• 75898-60-1 benzyloxycarbonyl-γ-benzyl-α-L-glutamyl-D-glutamine 
• 17080-13-6 -glutamin 
• 149-87-1 Pyroglutamic acid 
• 124-38-9 carbon dioxide 
• 107-12-0 propiononitrile 
• 5959-95-5 D-Glutamin 
• 56-85-9 L-glutamine 
• 28047-15-6 α-N-phenylacetyl-L-glutamine 
• 2650-69-3 glycyl=>glutaminyl=>glycine 
• 39537-23-0 alanyl-glutamine 
• 38062-69-0 leucyl-glutamine 

Relevant articles and documents

Single-Cell-Based Screening and Engineering of d -Amino Acid Amidohydrolases Using Artificial Amidophenol Substrates and Microbial Biosensors

Enantiomerically pure d-amino acids are important intermediates as chiral building blocks for peptidomimetics and semisynthetic antibiotics. Here, a transcriptional factor-based screening strategy was used for the rapid screening of d-stereospecific amino acid amidase via an enzyme-specific amidophenol substrate. We used a d-threonine amidophenyl derivative to produce 2-aminophenol that serves as a putative enzyme indicator in the presence of d-threonine amidases. Comparative analyses of known bacterial species indicated that several Bacillus strains produce amidase and form putative indicators in culture media. The estimated amidase was cloned and subjected to rapid directed evolution through biosensor cells. Consequently, we characterized the F119A mutation that significantly improved the catalytic activity toward d-alanine, d-threonine, and d-glutamate. Its beneficial effects were confirmed by higher conversions and recurrent applications of the mutant enzyme, compared to the wild-type. This study showed that rapid directed evolution with biosensors coupled to designed substrates is useful to develop biocatalytic processes.

Light-Driven Kinetic Resolution of α-Functionalized Carboxylic Acids Enabled by an Engineered Fatty Acid Photodecarboxylase

Chiral α-functionalized carboxylic acids are valuable precursors for a variety of medicines and natural products. Herein, we described an engineered fatty acid photodecarboxylase (CvFAP)-catalyzed kinetic resolution of α-amino acids and α-hydroxy acids, which provides the unreacted R-configured substrates with high yields and excellent stereoselectivity (ee up to 99 %). This efficient light-driven process requires neither NADPH recycling nor prior preparation of esters, which were required in previous biocatalytic approaches. The structure-guided engineering strategy is based on the scanning of large amino acids at hotspots to narrow the substrate binding tunnel. To the best of our knowledge, this is the first example of asymmetric catalysis by an engineered CvFAP.

SEPARATING AGENT AND MANUFACTURING METHOD THEREOF

An embodiment of the present invention is a separating agent wherein a group represented by a chemical formula of: or a group represented by a chemical formula of: is introduced on a surface thereof.