ContaminantDB: L-Glutamine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:21:45 UTC

Update Date

2026-05-14 16:24:09 UTC

Accession Number

CHEM003279

Identification

Common Name

L-Glutamine

Class

Small Molecule

Description

L-Glutamine (Gln) is one of the 20 amino acids encoded by the standard genetic code. Its side chain is an amide; it is formed by replacing a side-chain hydroxyl of glutamic acid with an amine functional group. glutamine is found in foods high in proteins, such as fish, red meat, beans, and dairy products. glutamine is a supplement that is used in weightlifting, bodybuilding, endurance and other sports, as well as by those who suffer from muscular cramps or pain particularly elderly people. The main use of glutamine within the diet of either group is as a means of replenishing the body's stores of amino acids that have been used during exercise or everyday activities. Studies which are looking into problems with excessive consumption of glutamine thus far have proved inconclusive. However, normal supplementation is healthy mainly because glutamine is supposed to be supplemented after prolonged periods of exercise (for example, a workout or exercise in which amino acids are required for use) and replenishes amino acid stores; this being the main reason glutamine is recommended during fasting or for people who suffer from physical trauma, immune deficiencies, or cancer. There is a significant body of evidence that links glutamine-enriched diets with intestinal effects; aiding maintenance of gut barrier function, intestinal cell proliferation and differentiation, as well as generally reducing septic morbidity and the symptoms of Irritable Bowel Syndrome. The reason for such cleansing properties is thought to stem from the fact that the intestinal extraction rate of glutamine is higher than that for other amino acids, and is therefore thought to be the most viable option when attempting to alleviate conditions relating to the gastrointestinal tract. These conditions were discovered after comparing plasma concentration within the gut between glutamine-enriched and non glutamine-enriched diets. However, even though glutamine is thought to have cleansing properties and effects, it is unknown to what extent glutamine has clinical benefits, due to the varied concentrations of glutamine in varieties of food. It is also known that glutamine has various effects in reducing healing time after operations. Hospital waiting times after abdominal surgery are reduced by providing parenteral nutrition regimens containing amounts of glutamine to patients. Clinical trials have revealed that patients on supplementation regimes containing glutamine have improved nitrogen balances, generation of cysteinyl-leukotrienes from polymorphonuclear neutrophil granulocytes and improved lymphocyte recovery and intestinal permeability (in postoperative patients) - in comparison to those who had no glutamine within their dietary regime; all without any side-effects. It is synthesized from glutamic acid and ammonia. It is the principal carrier of nitrogen in the body and is an important energy source for many cells.

Contaminant Sources

Cosmetic Chemicals
EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Feces
HMDB Contaminants - Urine
HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amine
Animal Toxin
Dietary Supplement
Drug
Food Toxin
Household Toxin
Metabolite
Micronutrient
Natural Compound
Non-Essential Amino Acid
Nutraceutical
Organic Compound
Supplement

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-2,5-Diamino-5-oxopentanoic acid	ChEBI
(2S)-2-Amino-4-carbamoylbutanoic acid	ChEBI
(S)-2,5-Diamino-5-oxopentanoic acid	ChEBI
Glutamic acid 5-amide	ChEBI
Glutamic acid amide	ChEBI
GLUTAMINE	ChEBI
L-(+)-Glutamine	ChEBI
L-2-Aminoglutaramic acid	ChEBI
L-Glutamic acid gamma-amide	ChEBI
L-Glutamin	ChEBI
L-Glutaminsaeure-5-amid	ChEBI
Levoglutamide	ChEBI
Q	ChEBI
Endari	Kegg
Nutrestore	Kegg
(2S)-2,5-Diamino-5-oxopentanoate	Generator
(2S)-2-Amino-4-carbamoylbutanoate	Generator
(S)-2,5-Diamino-5-oxopentanoate	Generator
Glutamate 5-amide	Generator
Glutamate amide	Generator
L-2-Aminoglutaramate	Generator
L-Glutamate g-amide	Generator
L-Glutamate gamma-amide	Generator
L-Glutamate γ-amide	Generator
L-Glutamic acid g-amide	Generator
L-Glutamic acid γ-amide	Generator
2-Aminoglutaramic acid	HMDB
Cebrogen	HMDB
gamma-Glutamine	HMDB
Glavamin	HMDB
Glumin	HMDB
L-2-Aminoglutaramidic acid	HMDB
L-Glutamic acid 5-amide	HMDB
L-Glutamid	HMDB
L-Glutamide	HMDB
Levoglutamid	HMDB
Levoglutamida	HMDB
Levoglutamidum	HMDB
Levoglutamina	HMDB
Polyglutamine	HMDB
Stimulina	HMDB
D-Glutamine	HMDB
D Glutamine	HMDB
L Glutamine	HMDB

Chemical Formula

C₅H₁₀N₂O₃

Average Molecular Mass

146.145 g/mol

Monoisotopic Mass

146.069 g/mol

CAS Registry Number

56-85-9

IUPAC Name

(2S)-2-amino-4-carbamoylbutanoic acid

Traditional Name

L-glutamine

SMILES

N[C@@H](CCC(N)=O)C(O)=O

InChI Identifier

InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1

InChI Key

ZDXPYRJPNDTMRX-VKHMYHEASA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Fatty acid
Amino acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

proteinogenic amino acid (CHEBI:18050 )
L-alpha-amino acid (CHEBI:18050 )
glutamine (CHEBI:18050 )
glutamine family amino acid (CHEBI:18050 )
Common amino acids (C00064 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Extracellular
Membrane
Mitochondria

Biofluid Locations

Not Available

Tissue Locations

Adipose Tissue
Fibroblasts
Gut
Intestine
Kidney
Muscle
Myelin
Neuron
Pancreas
Placenta
Prostate
Skeletal Muscle
Spleen
Stratum Corneum
Testes

Pathways

Name	SMPDB Link	KEGG Link
Amino Sugar Metabolism	SMP00045	map00520
Ammonia Recycling	SMP00009	map00910
Glutamate Metabolism	SMP00072	map00250
Phenylacetate Metabolism	SMP00126	map00360
Purine Metabolism	SMP00050	map00230
Pyrimidine Metabolism	SMP00046	map00240
Transcription/Translation	SMP00019	Not Available
Urea Cycle	SMP00059	Not Available
Citrullinemia Type I	SMP00001	Not Available
Ornithine Transcarbamylase Deficiency (OTC Deficiency)	SMP00205	Not Available
Propionic Acidemia	SMP00236	Not Available

Applications

nutraceutical

Biological Roles

Chemical Roles

EC 1.14.13.39 (nitric oxide synthase) inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	185.5 dec°C
Boiling Point	Not Available
Solubility	4.13E+004 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	97.8 g/L	ALOGPS
logP	-3.3	ALOGPS
logP	-4	ChemAxon
logS	-0.17	ALOGPS
pKa (Strongest Acidic)	2.15	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	106.41 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	33.11 m³·mol⁻¹	ChemAxon
Polarizability	13.87 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0a4i-0910000000-adb283bb40327f705680	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0a4i-0910000000-134e80840320dadf6ad1	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-05fr-7910000000-89f87d4acc18299244f5	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0a4i-0900000000-952a471cad5e5ead0a7e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-004i-1961000000-94183211889cfe72d4ff	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0a4i-1920000000-6505cd814f3707a0feba	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-004i-0692000000-9788416fdefb051b9586	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-adb283bb40327f705680	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-134e80840320dadf6ad1	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-QQ (Non-derivatized)	splash10-00dj-4921200000-5446333d9aa592da8a07	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-05fr-7910000000-89f87d4acc18299244f5	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4i-0900000000-952a471cad5e5ead0a7e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004i-1961000000-94183211889cfe72d4ff	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4i-1920000000-6505cd814f3707a0feba	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004i-0692000000-9788416fdefb051b9586	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-ce2b15fe45c57a30c6bb	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ab9-1900000000-7be5eab1056d2a249ab5	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0900000000-5dc2d147bea250c7b80e	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fb9-0921000000-5dcbab01982f543f7925	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004j-0940000000-102c9a43b5153f06927f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-716b1947d48f42862cdf	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9610000000-bfd7aa529a6e7f62de43	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0059-3900000000-c8f487d1a561e49327c0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-eee04836e7577e11d0d0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a59-9000000000-54ffbe5be8d7dbede389	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0900000000-79283391c985f8286677	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-9000000000-6afbd5929b6e2371a371	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-d5bd83614703b048228e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-dc8def340a2655f9a399	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0900000000-47e3e94a4387c53e0bd6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-9000000000-c1acfa3750a90d81ce15	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-0900000000-93f01bccbc98f18d4b07	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-ce03708ec9ce55cd8952	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0933201000-9339494cebedd9c39135	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0900000000-64561a4c3590d5994e37	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0900000000-fdcdd7591fb182d804e2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03dm-0030900000-66314ae704783630947a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0933100000-8798d2e46a415bb1029a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0900000000-dddea137e500a9b364cc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0900000000-a78f8e4b2d6b37917b21	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0920000000-8c6e1eb7de6f70911080	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-fa42fc4bcba608992804	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-2900000000-074610880ea19a417f60	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-059x-9200000000-8b7dae54eb8325667bd7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-e115d9215eea3f0c3629	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-55b1ac62eea66274b984	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001j-0900000000-c9c71895033d66cb2bec	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-bc4e294b8a3fd8c5abce	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Absorption is efficient and occurs by an active transport mechanism

Mechanism of Toxicity

Supplemental L-glutamine's possible immunomodulatory role may be accounted for in a number of ways. L-glutamine appears to play a major role in protecting the integrity of the gastrointestinal tract and, in particular, the large intestine. During catabolic states, the integrity of the intestinal mucosa may be compromised with consequent increased intestinal permeability and translocation of Gram-negative bacteria from the large intestine into the body. The demand for L-glutamine by the intestine, as well as by cells such as lymphocytes, appears to be much greater than that supplied by skeletal muscle, the major storage tissue for L-glutamine. L-glutamine is the preferred respiratory fuel for enterocytes, colonocytes and lymphocytes. Therefore, supplying supplemental L-glutamine under these conditions may do a number of things. For one, it may reverse the catabolic state by sparing skeletal muscle L-glutamine. It also may inhibit translocation of Gram-negative bacteria from the large intestine. L-glutamine helps maintain secretory IgA, which functions primarily by preventing the attachment of bacteria to mucosal cells. L-glutamine appears to be required to support the proliferation of mitogen-stimulated lymphocytes, as well as the production of interleukin-2 (IL-2) and interferon-gamma (IFN-gamma). It is also required for the maintenance of lymphokine-activated killer cells (LAK). L-glutamine can enhance phagocytosis by neutrophils and monocytes. It can lead to an increased synthesis of glutathione in the intestine, which may also play a role in maintaining the integrity of the intestinal mucosa by ameliorating oxidative stress. The exact mechanism of the possible immunomodulatory action of supplemental L-glutamine, however, remains unclear. It is conceivable that the major effect of L-glutamine occurs at the level of the intestine. Perhaps enteral L-glutamine acts directly on intestine-associated lymphoid tissue and stimulates overall immune function by that mechanism, without passing beyond the splanchnic bed.

Metabolism

Enterocytes, Hepatic

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Used for nutritional supplementation, also for treating dietary shortage or imbalance.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00130

HMDB ID

HMDB0000641

FooDB ID

FDB030965

Phenol Explorer ID

Not Available

KNApSAcK ID

BiGG ID

BioCyc ID

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Stephen Paul, “Novel preparation of fiber, L-glutamine and a soy derivative for the purpose of enhancement of isoflavone bioavailability.” U.S. Patent US20020076455, issued June 20, 2002.

MSDS

Link

General References

1. Jiao, Qingcai; Qian, Shaosong; Chen, Ran; Wu, Xiaoyan. Synthesis of L-glutamine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7 pp.

2. Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.

3. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.

4. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.

5. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386

6. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)

7. Jiao, Qingcai; Qian, Shaosong; Chen, Ran; Wu, Xiaoyan. Synthesis of L-glutamine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7 pp.

8. Szebenyi G, Morfini GA, Babcock A, Gould M, Selkoe K, Stenoien DL, Young M, Faber PW, MacDonald ME, McPhaul MJ, Brady ST: Neuropathogenic forms of huntingtin and androgen receptor inhibit fast axonal transport. Neuron. 2003 Sep 25;40(1):41-52.

9. Wada A, Yoshida R, Oda K, Fukuba E, Uchida N, Kitagaki H: Acute encephalopathy associated with intravenous immunoglobulin therapy. AJNR Am J Neuroradiol. 2005 Oct;26(9):2311-5.