D-Glutamic Acid

HCID 23327
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Basic information

CAS
6893-26-1
Standard SMILES
N[C@H](CCC(=O)O)C(=O)O
InChIKey
WHUUTDBJXJRKMK-GSVOUGTGSA-N
Molecular formula
C5H9NO4
Average molar mass
147.13 g/mol
Monoisotopic mass
147.05315777

Overview

D-glutamic acid is an optically active form of glutamic acid having D-configuration. It has a role as a mouse metabolite and an Escherichia coli metabolite. It is a D-alpha-amino acid and a glutamic acid. It is a conjugate acid of a D-glutamate(1-). It is an enantiomer of a L-glutamic acid.

Names & identifiers

Preferred name
D-Glutamic Acid
IUPAC
(2R)-2-aminopentanedioic acid
English name
D(-)-Glutamic acid
Molecular formula
C5H9NO4
Molecular weight
147.13

Names & synonyms

D-glutamic acid6893-26-1(2R)-2-aminopentanedioic acidD-glutamateD-GluD-Glutaminic acidD-2-Aminoglutaric acidDTXSID1048675Q479989WEADTXCID1028601CHEBI:15966NSC-77686
Show more names
D-GLUCURONOLACTONEd-glutamic(R)-GLUTAMIC ACID(R)-2-Aminoglutaric acid, (R)-2-Aminopentanedioic acid, D-Glu, R-(-)-1-Aminopropane-1,3-dicarboxylic acidNSC 77686
(-)-Glutamic acidD Glutamateglutamic acid d-RefChem:583854(2R)-2-azaniumyl-5-hydroxy-5-oxopentanoate230-000-8H-D-Glu-OH(R)-2-aminopentanedioic acid

Database identifiers

CAS
6893-26-1
PubChem CID
23327
DTXSID
DTXSID1048675
ChEMBL
CHEMBL76232
ChEBI
CHEBI:15966
UNII
Q479989WEA
EC Number
230-000-8
Nikkaji
J9.214B

Properties

Computed structural properties

XLogP
-3.7
Topological polar surface area
101 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
5
Rotatable bonds
4
Heavy atoms
10

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Amino Acids and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
Solubility8.88 mg/mL at 25 °C
Melting Point201 °C
Physical Description · 2 items

Shinny solid; [Merck Index] White crystalline powder; [Alfa Aesar MSDS]

Solid

Physicochemical properties

Melting point
200 · 200-202 °C (subl.)(lit.)
alpha
-31.3 · -31.3 º (c=10, 2 N HCl)
Boiling point
267.21 °C · 267.21°C (rough estimate)
Density
1.538 · 1.5380
refractive index
1.421 · 1.4210 (estimate)
storage temp.
Keep in dark place,Sealed in dry,Room Temperature

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 83.3% (5 of 6) of all reports.

Warning

H315 (16.7%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 6 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationD-Glutamic acid: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryMay cause irritation; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (16.7%)

Safety data

F
10
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
hs_code
29224200
risk_code
36/37/38

Chemistry & industry

Pharmacology

Tissue LocationsEpidermis
Cellular LocationsCytoplasm

Uses & manufacturing

UsesGlutamic acid is a non-essential amino acid and excitatory neurotransmitter; Used as a nutritional supplement; [Merck Index]
General Manufacturing InformationD-Glutamic acid: ACTIVE
Applications · 4 items

UsesD-Glutamic Acid is the unnatural (R)-enantiomer of Glutamic Acid, a non-essential amino acid. Its salt form (glutamate) is an important neurotransmitter that plays a key role in long-term potentiation and is important for learning and memory. Glutamic Acid is also a key molecule in cellular metabolism.

UsesD-Glutamic acid acts as a superior to alpha ketoglutarate. It helps in the growth of Lactobacillus arabinosus. It can inhibit the IgE binding to peanut allergens. It is widely used in pharmaceuticals and foods.

UsesD-glutamic acid is suitable for use in the structure-affinity relationship (SAR)-study of GR (glutamate racemase) enzyme and its inhibitors.

General DescriptionD-Glutamic acid is an essential constituent of the bacterial peptidoglycan structure. It is added to UDP-N-acetylmuramyl-L-alanine (UDP-MurNAc-L-alanine) by the enzyme D-glutamic acid-adding enzyme (murD). This is, then, incorporated into the peptidoglycan precursor. Peptidoglycan makes up the cell walls of Gram-positive and -negative bacteria. The conversion of L-glutamate to D-glutamate by glutamate racemase (GR) enzyme is an essential step in the synthesis of peptidoglycan.

Upstream & downstream products

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]

Additional notes

DefinitionChEBI: An optically active form of glutamic acid having D-configuration.

Related reactions

34 records
New reaction record

Compound notes

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