Aspartic acid

Aspartic acid
Names


IUPAC names Trivial: Aspartic acid Systematic: 2-Aminobutanedioic acid
Other names Aminosuccinic acid, asparagic acid, asparaginic acid^[1]
Identifiers
CAS Number	617-45-8^Y 56-84-8 (L-isomer)^N 1783-96-6 (D-isomer)^N
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:22660^Y
ChemSpider	411^Y
ECHA InfoCard	100.000.265
EC Number	200-291-6
KEGG	C16433^Y
PubChem CID	424
UNII	28XF4669EP^Y
InChI InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)^Y Key: CKLJMWTZIZZHCS-UHFFFAOYSA-N^Y InChI=1/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9) Key: CKLJMWTZIZZHCS-UHFFFAOYAE
SMILES O=C(O)CC(N)C(=O)O C(C(C(=O)O)N)C(=O)O
Properties
Chemical formula	C₄H₇NO₄
Molar mass	133.10 g·mol⁻¹
Appearance	colourless crystals
Density	1.7 g/cm³
Melting point	270 °C (518 °F; 543 K)
Boiling point	324 °C (615 °F; 597 K) (decomposes)
Solubility in water	4.5 g/L^[2]
Acidity (pK_a)	3.9
Magnetic susceptibility (χ)	-64.2·10⁻⁶ cm³/mol
Hazards
Safety data sheet	See: data page
NFPA 704	1 1 0
Supplementary data page
Structure and properties	Refractive index (n), Dielectric constant (ε_r), etc.
Thermodynamic data	Phase behaviour solid–liquid–gas
Spectral data	UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Aspartic acid (abbreviated as Asp or D; encoded by the codons [GAU and GAC]), also known as aspartate, is an α-amino acid that is used in the biosynthesis of proteins.^[3] Similar to all other amino acids it contains an amino group and a carboxylic acid. Its α-amino group is in the protonated –NH+
3 form under physiological conditions, while its α-carboxylic acid group is deprotonated −COO⁻ under physiological conditions. Aspartic acid has an acidic side chain (CH₂COOH) which reacts with other amino acids, enzymes and proteins in the body.^[3] Under physiological conditions (pH 7.4) in proteins the side chain usually occurs as the negatively charged aspartate form, −COO⁻ .^[3] It is a non-essential amino acid in humans, meaning the body can synthesize it as needed.

D-Aspartate is one of two D-amino acids commonly found in mammals.^[3].

In proteins aspartate sidechains are often hydrogen bonded to form asx turns or asx motifs, which frequently occur at the N-termini of alpha helices.

Asp's L-isomer is one of the 22 proteinogenic amino acids, i.e., the building blocks of proteins. Asp (and glutamic acid) is classified as acidic, with a pK_a of 3.9, however in a peptide this is highly dependent on the local environment (as with all amino acids), and could be as high as 14. Asp is pervasive in biosynthesis.

Discovery

Aspartic acid was first discovered in 1827 by Auguste-Arthur Plisson and Étienne Ossian Henry^[4] by hydrolysis of asparagine, which had been isolated from asparagus juice in 1806.^[5] Their original method used lead hydroxide, but various other acids or bases are more commonly used instead.

Forms and nomenclature

There are two forms or enantiomers of aspartic acid. The name "aspartic acid" can refer to either enantiomer or a mixture of two.^[6] Of these two forms, only one, "L-aspartic acid", is directly incorporated into proteins. The biological roles of its counterpart, "D-aspartic acid" are more limited. Where enzymatic synthesis will produce one or the other, most chemical syntheses will produce both forms, "DL-aspartic acid," known as a racemic mixture.

Biosynthesis

Because Aspartate can be synthesized by the body it is classified as a non-essential amino acid. In the human body, aspartate is most frequently synthesized through the transamination of oxaloacetate. The biosynthesis of aspartate is facilitated by an aminotransferase enzyme: the transfer of an amine group from another molecule such as alanine or glutamine yields aspartate and an alpha-keto acid.^[3]

Aspartate is also a byproduct of the urea cycle.

Chemical synthesis

Racemic aspartic acid can be synthesized from diethyl sodium phthalimidomalonate, (C₆H₄(CO)₂NC(CO₂Et)₂).^[7]

The major disadvantage of the above technique is that equimolar amounts of each enantiomer are made. Using biotechnology it is now possible to use immobilised enzymes to create just one type of enantiomer owing to their stereospecificity.

Metabolism

In plants and microorganisms, aspartate is the precursor to several amino acids, including four that are essential for humans: methionine, threonine, isoleucine, and lysine. The conversion of aspartate to these other amino acids begins with reduction of aspartate to its "semialdehyde," O₂CCH(NH₂)CH₂CHO.^[8] Asparagine is derived from aspartate via transamidation:

-O₂CCH(NH₂)CH₂CO₂- + GC(O)NH₃+ O₂CCH(NH₂)CH₂CONH₃+ + GC(O)O

(where GC(O)NH₂ and GC(O)OH are glutamine and glutamic acid, respectively)

Participation in the urea cycle

In the urea cycle, aspartate and ammonia donate amino groups leading to the formation of urea.

Other biochemical roles

Aspartate has many other biochemical roles. It is a metabolite in the urea cycle and participates in gluconeogenesis. It carries reducing equivalents in the malate-aspartate shuttle, which utilizes the ready interconversion of aspartate and oxaloacetate, which is the oxidized (dehydrogenated) derivative of malic acid. Aspartate donates one nitrogen atom in the biosynthesis of inosine, the precursor to the purine bases. In addition, aspartic acid acts as hydrogen acceptor in a chain of ATP synthase.

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles. ^{[§ 1]}

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|{{{bSize}}}px|alt=Glycolysis and Gluconeogenesis edit]]

Glycolysis and Gluconeogenesis edit

↑ The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".

Neurotransmitter

Aspartate (the conjugate base of aspartic acid) stimulates NMDA receptors, though not as strongly as the amino acid neurotransmitter L-glutamate does.^[9]

Applications & market

As of 2014, the global market for aspartic acid is $117MM annually (50-60K MT/Yr)^[10] with potential areas of growth accounting for an addressable market of $8.78BB.^[11] The three largest market segments include the U.S., Western Europe, and China. Current applications include biodegradable polymers (polyaspartic acid), low calorie sweeteners (aspartame), scale and corrosion inhibitors, and resins.

Nearly all aspartic acid is manufactured in China.

Superabsorbent polymers

One area of aspartic acid market growth is biodegradable superabsorbent polymers (SAP). The superabsorbent polymers market is anticipated to grow at a CAGR of 5.5% from 2014 to 2019 to reach a value of $8.78BB globally.^[11] Around 75% of superabsorbent polymers are used in disposable diapers and an additional 20% is used for adult incontinence and feminine hygiene products. Polyaspartic acid, the polymerization product of aspartic acid, is a biodegradable substitute to polyacrylate.^[12] The polyaspartate market comprises a small fraction (est. < 1%) of the total SAP market.

Additional uses

In addition to SAP, aspartic acid has applications in the $19B fertilizer industry, where polyaspartate improves water retention and nitrogen uptake;^[13] the $1.1B (2020) concrete floor coatings market, where polyaspartic is a low VOC, low energy alternative to traditional epoxy resins;^[14] and lastly the >$5B scale and corrosion inhibitors market.^[15]

Sources

Dietary sources

Aspartic acid is not an essential amino acid, which means that it can be synthesized from central metabolic pathway intermediates in humans. However, aspartic acid is found in:

Animal sources: oysters, luncheon meats, sausage meat, wild game
Vegetable sources: sprouting seeds, oat flakes, avocado,^[16] asparagus,^[17] young sugarcane, and molasses from sugar beets.^[1]
Dietary supplements, either as aspartic acid itself or salts (such as magnesium aspartate)
The sweetener aspartame, an alanine-aspartate dimer (brands: NutraSweet, Equal, Canderel, etc.)

References

1 2 "862. Aspartic acid". The Merck Index (11th ed.). 1989. p. 132. ISBN 0-911910-28-X.
↑ "ICSC 1439 - L-ASPARTIC ACID". inchem.org.
1 2 3 4 G.,, Voet, Judith; W.,, Pratt, Charlotte. Fundamentals of biochemistry : life at the molecular level. ISBN 9781118918401. OCLC 910538334.
↑ Berzelius JJ, Öngren OG (1839). Traité de chimie (in French). 3. Brussels: A. Wahlen et Cie. p. 81. Retrieved 25 August 2015.
↑ Plimmer R (1912) [1908]. Plimmer R, Hopkins F, eds. The chemical composition of the proteins. Monographs on Biochemistry. Part I. Analysis (2nd ed.). London: Longmans, Green and Co. p. 112. Retrieved January 18, 2010.
↑ "Nomenclature and symbolism for amino acids and peptides (IUPAC-IUB Recommendations 1983)", Pure Appl. Chem., 56 (5): 595–624, 1984, doi:10.1351/pac198456050595 .
↑ Dunn MS, Smart BW (1950). "DL-Aspartic Acid". Org. Synth. 30: 7. ; Coll. Vol., 4, p. 55 .
↑ Lehninger AL, Nelson DL, Cox MM (2000). Principles of Biochemistry (3rd ed.). New York: W. H. Freeman. ISBN 1-57259-153-6.
↑ Chen PE, Geballe MT, Stansfeld PJ, Johnston AR, Yuan H, Jacob AL, Snyder JP, Traynelis SF, Wyllie DJ (May 2005). "Structural features of the glutamate binding site in recombinant NR1/NR2A N-methyl-D-aspartate receptors determined by site-directed mutagenesis and molecular modeling". Molecular Pharmacology. 67 (5): 1470–84. PMID 15703381. doi:10.1124/mol.104.008185.
↑ Evans J (2014). Commercial Amino Acids. BCC Research. pp. 101–103.
1 2 Transparency Market Research. Superabsorbent polymers market - global industry analysis, size, share, growth, trends and forecase, 2014-2020. (2014).
↑ Alford DD, Wheeler AP, Pettigrew CA (1994). "Biodegradation of thermally synthesized polyaspartate". J Environ Polym Degr. 2: 225–236.
↑ Kelling K (2001). Crop Responses to Amisorb in the North Central Region. University of Wisconsin-Madison.
↑ Global concrete floor coatings market will be worth US$1.1 bn by 2020. Transparency Market Research (2015).
↑ Corrosion inhibitors market analysis by product, by application, by end-use industry, and segment forecasts to 2020. Grand View Research (2014)
↑ Salunkhe DK, Kadam S (18 August 1995). Handbook of Fruit Science and Technology: Production, Composition, Storage, and Processing. CRC Press. pp. 368–. ISBN 978-0-8247-9643-3.
↑ Considine DM (6 December 2012). Foods and Food Production Encyclopedia. Springer Science & Business Media. pp. 114–. ISBN 978-1-4684-8511-0.

External links

GMD MS Spectrum
American Chemical Society (21 April 2010). "Ancestral Eve' Crystal May Explain Origin of Life's Left-Handedness". ScienceDaily. Archived from the original on 23 April 2010. Retrieved 2010-04-21.

Other hematological agents

Antianemic
preparations
(B03)

Erythropoietins	Darbepoetin alfa Methoxy polyethylene glycol-epoetin beta Peginesatide
Iron supplements	Ferrous ascorbate Ferrous aspartate Ferrous carbonate Ferrous chloride Ferrous fumarate Ferrous gluconate Ferrous glycine sulfate Ferrous iodine Ferrous succinate Ferrous sulfate Ferrous tartrate Iron sucrose Sodium ferric gluconate complex

Blood substitutes and
perfusion solutions (B05)

Dextran
Gelatin agents
Hemoglobin crosfumaril
Hemoglobin raffimer
Hydroxyethyl starch
Icodextrin
Mannitol
Serum albumin
Sorbitol

Enzymes (B06AA)

Drugs used i hereditary
angioedema (B06AC)

The encoded amino acid

General topics

By properties

Aliphatic	Branched-chain amino acids (Valine Isoleucine Leucine) Methionine Alanine Proline Glycine
Aromatic	Phenylalanine Tyrosine Tryptophan Histidine
Polar, uncharged	Asparagine Glutamine Serine Threonine
Positive charge (pK_a)	Lysine (≈10.8) Arginine (≈12.5) Histidine (≈6.1)
Negative charge (pK_a)	Aspartic acid (≈3.9) Glutamic acid (≈4.1) Cysteine (≈8.3) Tyrosine (≈10.1)

Other classifications

Neurotransmitters
Amino acid-derived	Major excitatory/inhibitory systems: Glutamate system: Agmatine Aspartic acid (aspartate) Cycloserine Glutamic acid (glutamate) Glutathione Glycine GSNO GSSG Kynurenic acid NAA NAAG Proline Serine; GABA system: GABA GABOB GHB; Glycine system: α-Alanine β-Alanine Glycine Hypotaurine Proline Sarcosine Serine Taurine; GHB system: GHB T-HCA (GHC) Biogenic amines: Monoamines: 6-OHM Dopamine Epinephrine (adrenaline) NAS (normelatonin) Norepinephrine (noradrenaline) Serotonin (5-HT); Trace amines: 3-Iodothyronamine N-Methylphenethylamine N-Methyltryptamine m-Octopamine p-Octopamine Phenylethanolamine Phenethylamine Synephrine Tryptamine m-Tyramine p-Tyramine; Others: Histamine Neuropeptides: See here instead.
Lipid-derived	Endocannabinoids: 2-AG 2-AGE (noladin ether) 2-ALPI 2-OG AA-5-HT Anandamide (AEA) DEA LPI NADA NAGly OEA Oleamide PEA RVD-Hpα SEA Virodhamine (O-AEA) Neurosteroids: See here instead.
Nucleobase-derived	Nucleosides: Adenosine system: Adenosine ADP AMP ATP
Vitamin-derived	Cholinergic system: Acetylcholine
Miscellaneous	Gasotransmitters: Carbon monoxide (CO) Hydrogen sulfide (H₂S) Nitric oxide (NO); Candidates: Acetaldehyde Ammonia (NH₃) Carbonyl sulfide (COS) Nitrous oxide (N₂O) Sulfur dioxide (SO₂)

Glutamate receptor modulators

Receptor
(ligands)

Ionotropic

AMPA	Agonists: Glutamate/active site agonists: 5-Fluorowillardiine Acromelic acid (acromelate) AMPA BOAA Domoic acid Glutamate Ibotenic acid Proline Quisqualic acid Willardiine; Positive allosteric modulators: Aniracetam Cyclothiazide CX-516 CX-546 CX-614 Farampator (CX-691, Org 24448) CX-717 CX-1739 CX-1942 Diazoxide Hydrochlorothiazide (HCTZ) IDRA-21 LY-392,098 LY-404,187 LY-451,646 LY-503,430 Mibampator (LY-451,395) Org 26576 Oxiracetam PEPA PF-04958242 Piracetam Pramiracetam S-18986 S-47445 (CX-1632) Sunifiram Unifiram Antagonists: ACEA-1011 ATPO Becampanel Caroverine CNQX Dasolampanel DNQX Fanapanel (MPQX) GAMS GYKI-52466 Kaitocephalin Kynurenic acid Kynurenine Licostinel (ACEA-1021) NBQX PNQX Selurampanel Tezampanel Theanine Topiramate YM90K Zonampanel; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental) Cyclopropane Enflurane Ethanol Evans blue GYKI-53,655 Halothane Irampanel Isoflurane Perampanel Pregnenolone sulfate Talampanel
NMDA	Agonists: Glutamate/active site agonists: AMAA Aspartate Glutamate Homocysteic acid (L-HCA) Homoquinolinic acid Ibotenic acid NMDA Proline Quinolinic acid Tetrazolylglycine Theanine; Glycine site agonists: β-Fluoro-D-alanine ACBD ACC (ACPC) ACPD AK-51 Apimostinel (NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687,414 L-Alanine L-Serine Milacemide Neboglamine (nebostinel) Rapastinel (GLYX-13) Sarcosine; Polyamine site agonists: Spermidine Spermine; Other positive allosteric modulators: 24S-Hydroxycholesterol DHEA DHEA sulfate Pregnenolone sulfate SAGE-718 Antagonists: Competitive antagonists: AP5 (APV) AP7 CGP-37849 CGP-39551 CGP-39653 CGP-40116 CGS-19755 CPP Kaitocephalin LY-233,053 LY-235,959 LY-274,614 MDL-100,453 Midafotel (d-CPPene) NPC-12,626 NPC-17,742 PBPD PEAQX Perzinfotel PPDA SDZ-220581 Selfotel; Noncompetitive antagonists: ARR-15,896 Caroverine Dexanabinol FPL-12495 FR-115,427 Hodgkinsine Magnesium MDL-27,266 NPS-1506 Psychotridine Zinc; Uncompetitive pore blockers: 2-MDP 3-HO-PCP 3-MeO-PCE 3-MeO-PCMo 3-MeO-PCP 4-MeO-PCP 8A-PDHQ 18-MC α-Endopsychosin Alaproclate Amantadine Aptiganel Arketamine ARL-12,495 ARL-15,896-AR ARL-16,247 Budipine Conaridine Delucemine Dexoxadrol Dextrallorphan Dieticyclidine Diphenidine Dizocilpine Ephenidine Esketamine Etoxadrol Eticyclidine Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Loperamide Memantine Methadone (Levomethadone) Methorphan (Dextromethorphan Levomethorphan) Methoxetamine Methoxphenidine Milnacipran Morphanol (Dextrorphan Levorphanol) NEFA Neramexane Nitromemantine Nitrous oxide Noribogaine Norketamine Orphenadrine PCPr PD-137889 Pethidine (meperidine) Phencyclamine Phencyclidine Propoxyphene Remacemide Rhynchophylline Rimantadine Rolicyclidine Sabeluzole Tabernanthine Tenocyclidine Tiletamine Tramadol Xenon; Glycine site antagonists: 4-Cl-KYN (AV-101) 5,7-DCKA 7-CKA ACC ACEA-1011 ACEA-1328 AV-101 Carisoprodol CGP-39653 CNQX DNQX Felbamate Gavestinel GV-196,771 Kynurenic acid Kynurenine L-689,560 L-701,324 Licostinel (ACEA-1021) LU-73,068 MDL-105,519 Meprobamate MRZ 2/576 PNQX ZD-9379; NR2B subunit antagonists: Besonprodil CERC-301 (MK-0657) CO-101,244 (PD-174,494) Eliprodil Haloperidol Ifenprodil Isoxsuprine Nylidrin Ro8-4304 Ro25-6981 Traxoprodil; Polyamine site antagonists: Arcaine Co 101676 Diaminopropane Diethylenetriamine Huperzine A Putrescine Ro 25-6981; Unclassified/unsorted antagonists: Bumetanide Chloroform Cyclopropane D-αAA Diethyl ether Enflurane Ethanol Flufenamic acid Flupirtine Furosemide Halothane Isoflurane Metaphit Methoxyflurane Niflumic acid Pentamidine isethionate Piretanide Toluene Transcrocetin (saffron) Trichloroethane Trichloroethanol Trichloroethylene Xylene
Kainate	Agonists: Glutamate/active site agonists: 5-Bromowillardiine 5-Iodowillardiine Acromelic acid (acromelate) AMPA ATPA Domoic acid Glutamate Ibotenic acid Kainic acid LY-339,434 Proline Quisqualic acid SYM-2081; Positive allosteric modulators: Cyclothiazide Diazoxide Enflurane Halothane Isoflurane Antagonists: ACEA-1011 CNQX Dasolampanel DNQX GAMS Kaitocephalin Kynurenic acid Licostinel (ACEA-1021) LY-382,884 NBQX NS102 Selurampanel Tezampanel Theanine Topiramate UBP-302; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental) Enflurane Ethanol Evans blue NS-3763 Pregnenolone sulfate

Metabotropic

mGluR₁	Agonists: ACPD DHPG Glutamate Ibotenic acid Quisqualic acid Ro01-6128 Ro67-4853 Ro67-7476 VU-71 Theanine Antagonists: BAY 36-7620 CPCCOEt Cyclothiazide LY-367,385 LY-456,236 MCPG NPS-2390
mGluR₂	Agonists: BINA CBiPES DCG-IV Eglumegad Glutamate Ibotenic acid LY-379,268 LY-404,039 (pomaglumetad) LY-487,379 LY-566,332 MGS-0028 Pomaglumetad methionil (LY-2140023) Talaglumetad; Positive allosteric modulators: JNJ-40411813 (ADX-71149) Antagonists: APICA CECXG EGLU HYDIA LY-307,452 LY-341,495 MCPG MGS-0039 PCCG-4; Negative allosteric modulators: Decoglurant RO4491533
mGluR₃	Agonists: CBiPES DCG-IV Eglumegad Glutamate Ibotenic acid LY-379,268 LY-404,039 (pomaglumetad) LY-487,379 MGS-0028 Pomaglumetad methionil (LY-2140023) Talaglumetad Antagonists: APICA CECXG EGLU HYDIA LY-307,452 LY-341,495 MCPG MGS-0039; Negative allosteric modulators: Decoglurant RO4491533
mGluR₄	Agonists: Glutamate L-AP4 PHCCC VU-001,171 VU-0155,041; Positive allosteric modulators: MPEP Antagonists: CPPG MAP4 MPPG MSOP MTPG UBP-1112
mGluR₅	Agonists: ACPD ADX-47273 CDPPB CHPG DFB DHPG Glutamate Ibotenic acid Quisqualic acid VU-1545 Antagonists: CTEP DMeOB LY-344,545 Mavoglurant MCPG NPS-2390 Remeglurant SIB-1757 SIB-1893; Negative allosteric modulators: Basimglurant Dipraglurant Fenobam GRN-529 MPEP MTEP Raseglurant
mGluR₆	Agonists: Glutamate L-AP4 Antagonists: CPPG MAP4 MPPG MSOP MTPG UBP-1112
mGluR₇	Agonists: AMN082 Glutamate L-AP4 Antagonists: CPPG MAP4 MMPIP MPPG MSOP MTPG UBP-1112
mGluR₈	Agonists: DCPG Glutamate L-AP4 Antagonists: CPPG MAP4 MPPG MSOP MTPG UBP-1112

Transporter
(blockers)

EAATs

Amphetamine
Aspartic acid (aspartate)
cis-ACBD
DHKA
Glutamic acid (glutamate)
HIP-A
HIP-B
Kainic acid
L-(-)-threo-3-Hydroxyaspartic acid
L-αAA
L-CCG-III ((2S,3S,4R)-CCG)
L-Serine-O-sulphate (SOS)
L-trans-2,4-PDC
MPDC
SYM-2081
TBOA
TFB-TBOA
Theanine
threo-3-Methylglutamic acid
UCPH-101
WAY-213,613

vGluTs

4-Methylene-L-glutamate
6-(4'-Phenylstyryl)-QDC
6-Biphenyl-4-yl-QDC
7-CKA
Acid red 114
Amido black 10B (naphthol blue black)
Bafilomycin A1
Benzopurpurin 4B
Bumetamide
Chicago sky blue 6B
Aspartic acid (aspartate)
DIDS
Direct blue 71
Erythro-4-methyl-L-glutamic acid
Evans blue
Furosemide
Glutamic acid (glutamate)
Kynurenic acid
Nigericin
NPPB (N144)
Ponceau SS
Reactive blue 2
Rose bengal
SITS
trans-ACDP
Trypan blue
Valinomycin
Xanthurenic acid

Enzyme
(inhibitors)

GAH	BPTES CB-839 DON
AST	2-Amino-3-butenoic acid AAOA AMB β-DL-Methylene-aspartate Hydrazinosuccinate
ALT	β-Chloro-L-alanine L-Cycloserine Propargylglycine
GDH	AAOA Bithionol Chloroquine EGCG GTP GW5074 Hexachlorophene Hydroxylamine Palmitoyl-CoA Pyridoxal phosphate
GS	2-Aminoadipic acid JFD01307SC Methionine sulfoximine Phosphinothricin (glufosinate)
GAD	3-Mercaptopropionic acid AAOA L-Allylglycine Semicarbazide

Others

Precursors: GHB
L-Glutamine

Prodrugs: Aceglutamide (to L-glutamine)

See also: Receptor/signaling modulators • GABAergics • GHBergics • Glycinergics

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