Need Assistance?

US & Canada:
+
UK: +

FAQs

Resources

Our Highlights

GMP Grade Efficient workshop for GMP production.
Optimal Prices Buying products on this site guarantees the best price!
Commercial Batches Independent GMP manufacturing suites that handle commercial batches
Prompt Delivery Warehouses in multiple cities to ensure timely delivery
Flexible Quantity Quantities available from milligrams to ton

Application Area

D-Glutamic acid

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

D-Glutamic acid is a non-essential amino acid acting at NMDA receptors. D-Glutamic is less active than the L-isomer.

Category

D-Amino Acids

Catalog number

BAT-008125

CAS number

6893-26-1

Molecular Formula

C5H9NO4

Molecular Weight

147.13

IUPAC Name

(2R)-2-aminopentanedioic acid

Synonyms

(R)-1-Aminopropane-1,3-dicarboxylic acid; (2R)-2-aminopentanedioic acid

Appearance

White powder

Purity

99%

Density

1.409 g/cm3

Melting Point

205°C (dec)

Boiling Point

333.8°C at 760 mmHg

Storage

Store at RT

Solubility

Soluble in Water

InChI

InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m1/s1

InChI Key

WHUUTDBJXJRKMK-GSVOUGTGSA-N

Canonical SMILES

C(CC(=O)O)C(C(=O)O)N

D-Glutamic acid is a stereoisomer of the naturally occurring L-glutamic acid, an amino acid that plays a crucial role in protein synthesis and metabolism. As a key component of the glutamate neurotransmitter system, D-glutamic acid is less common in nature but is often synthesized for use in various biochemical applications. It is known for its ability to function as a building block in peptide synthesis and as a reagent in the modification of other biochemical compounds. This compound's unique stereochemistry and reactivity make it a valuable tool in scientific research and industrial processes.

One of the primary applications of D-glutamic acid is in the synthesis of peptides and proteins. Due to its structural similarity to L-glutamic acid, D-glutamic acid can be incorporated into peptides to study their functional properties or to create modified peptides with enhanced stability or altered activity. It is also used in the synthesis of cyclic peptides, which are important in pharmaceutical development. By incorporating D-glutamic acid into peptide sequences, researchers can explore new types of peptides with specialized roles in biochemistry and medicine.

Another key application of D-glutamic acid is in the production of prodrugs. A prodrug is an inactive compound that can be metabolized into an active drug once inside the body. D-glutamic acid can be used in the design of prodrugs where it helps to enhance solubility or optimize the drug’s pharmacokinetic properties. By modifying drugs with D-glutamic acid, it is possible to improve their bioavailability, targeting, and efficacy in treating various diseases. This application is particularly important in the development of therapeutic agents for conditions with specific drug delivery needs.

D-glutamic acid is also utilized in the field of neurochemistry, particularly in the study of neurotransmitter systems. As a component of the glutamate pathway, D-glutamic acid is involved in processes related to synaptic transmission, learning, and memory. Researchers use D-glutamic acid to investigate the role of glutamate receptors and neurotransmission in the brain. This research is valuable in understanding neurological diseases such as Alzheimer's, Parkinson's, and other cognitive disorders, where glutamate signaling is often disrupted.

Finally, D-glutamic acid is explored for its role in the synthesis of biodegradable polymers. Polymers derived from glutamic acid derivatives have applications in drug delivery systems, medical devices, and tissue engineering. By incorporating D-glutamic acid into polymeric materials, it is possible to design biocompatible and environmentally friendly alternatives to traditional plastics. These polymers can be tailored for specific applications, offering potential advancements in both the medical and environmental sectors.

1.A possible link between parathyroid hormone secretion and local regulation of GABA in human parathyroid adenomas.

Ram Hong A1, Kim YA2,3, Hyun Bae J1, Sook Min H3, Hee Kim J1, Soo Shin C1, Yeon Kim S1, Kim SW1,4. J Clin Endocrinol Metab. 2016 Apr 12:jc20154329. [Epub ahead of print]

CONTEXT: Gamma-aminobutyric acid-B receptor 1 (GABABR1) forms a heterodimeric complex with calcium-sensing receptor (CaSR) in human brain tissue. However, the expression and implication of GABABR1 in human parathyroid adenoma has not yet been examined.

2.Design, synthesis and biological evaluation of 6-substituted pyrrolo[2,3-d]pyrimidines as dual inhibitors of TS and AICARFTase and as potential antitumor agents.

Liu Y1, Li M2, Zhang H2, Yuan J2, Zhang C2, Zhang K2, Guo H1, Zhao L1, Du Y2, Wang L3, Ren L4. Eur J Med Chem. 2016 Jun 10;115:245-56. doi: 10.1016/j.ejmech.2016.03.032. Epub 2016 Mar 21.

A new series of 2-amino-4-oxo-6-substituted pyrrolo[2,3-d]pyrimidines, with an isosteric replacement of the side chain amide moiety to a sulfur atom, were designed and synthesized as multitargeted antifolates as well as potential antitumor agents. Starting from previously synthesized 2-amino-4-oxo-pyrrolo[2,3-d]pyrimidin-6-yl-acetic acid, a reduction by lithium triethylborohydride and successive mesylation afforded the key mesylate. Nucleophilic substitution by mercaptoacetic or mercaptopropionic acid methyl esters, followed by hydrolysis and condensation with pyridinyl-methylamines provided the nonclassical compounds 1-6, whereas condensation with glutamic acid diethyl ester hydrochloride and saponification afforded the classical analogs 7-8. All target compounds exhibited inhibitory activities toward KB, SW620 and A549 tumor cell lines. The most potent compounds of this series, 7 and 8, are better inhibitors against A549 cells than methotrexate (MTX) and pemetrexed (PMX).

3.Immunization with a novel Clostridium perfringens epsilon toxin mutant rETX(Y196E)-C confers strong protection in mice.

Yao W1, Kang J1, Kang L1, Gao S1, Yang H1, Ji B1, Li P1, Liu J1, Xin W1, Wang J1. Sci Rep. 2016 Apr 6;6:24162. doi: 10.1038/srep24162.

Epsilon toxin (ETX) is produced by toxinotypes B and D of Clostridium perfringens. It can induce lethal enterotoxemia in domestic animals, mainly in sheep, goats and cattle, causing serious economic losses to global animal husbandry. In this study, a novel and stable epsilon toxin mutant rETX(Y196E)-C, obtained by substituting the 196th tyrosine (Y196) with glutamic acid (E) and introducing of 23 amino acids long C-terminal peptide, was determined as a promising recombinant vaccine candidate against enterotoxemia. After the third vaccination, the antibody titers against recombinant wild type (rETX) could reach 1:10(5) in each immunized group, and the mice were completely protected from 100 × LD50 (50% lethal dose) of rETX challenge. The mice in 15 μg subcutaneously immunized group fully survived at the dose of 500 × LD50 of rETX challenge and 80% of mice survived at 180 μg (1000 × LD50) of rETX administration. In vitro, immune sera from 15 μg subcutaneously immunized group could completely protect MDCK cells from 16 × CT50 (50% lethal dose of cells) of rETX challenge and protect against 10 × LD50 dose (1.

4.Neuronal antibodies in pediatric epilepsy: Clinical features and long-term outcomes of a historical cohort not treated with immunotherapy.

Wright S1, Geerts AT2, Jol-van der Zijde CM3, Jacobson L1, Lang B1, Waters P1, van Tol MJ3, Stroink H4, Neuteboom RF2, Brouwer OF5, Vincent A1. Epilepsia. 2016 Mar 21. doi: 10.1111/epi.13356. [Epub ahead of print]

OBJECTIVE: In autoimmune encephalitis the etiologic role of neuronal cell-surface antibodies is clear; patients diagnosed and treated early have better outcomes. Neuronal antibodies have also been described in patients with pediatric epilepsy without encephalitis. The aim was to assess whether antibody presence had any effect on long-term outcomes in these patients.