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

(3R)-3-Hydroxy-L-aspartic acid hydrochloride

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

Category

L-Amino Acids

Catalog number

BAT-016001

CAS number

1848942-27-7

Molecular Formula

C4H8ClNO5

Molecular Weight

185.56

IUPAC Name

(2S,3R)-2-amino-3-hydroxybutanedioic acid;hydrochloride

Synonyms

(2S,3R)-2-Amino-3-hydroxysuccinic acid hydrochloride; H-Asp(3R-OH)-OH.HCl; [L-erythro(2S,3R)]-3-Hydroxyaspartic acid hydrochloride; L-Aspartic acid, 3-hydroxy-, hydrochloride (1:1), (3R)-

Related CAS

7298-98-8 (free base)

Purity

≥95%

InChI

InChI=1S/C4H7NO5.ClH/c5-1(3(7)8)2(6)4(9)10;/h1-2,6H,5H2,(H,7,8)(H,9,10);1H/t1-,2+;/m0./s1

InChI Key

CNSCFTFKMPWXOF-FCIMFNEVSA-N

Canonical SMILES

C(C(C(=O)O)O)(C(=O)O)N.Cl

3R-3-Hydroxy-L-aspartic acid hydrochloride is a chemical compound belonging to the class of amino acids, specifically a derivative of aspartic acid. As an amino acid derivative, it is structurally modified to include a hydroxyl group, enhancing its chemical properties and potential biological activities. The hydrochloride form of this compound is a salt, which improves its solubility in water and therefore its utility in various biochemical applications. Its functional groups grant the molecule unique reactive properties, making it an interesting subject for biochemical research and potential applications in pharmaceuticals, agriculture, and materials science.

One key application of 3R-3-Hydroxy-L-aspartic acid hydrochloride is in the field of pharmaceuticals. Amino acid derivatives like this are often studied for their role in metabolic pathways and their potential to act as therapeutic agents. They can serve as building blocks for the synthesis of peptide-based drugs or as intermediates in drug synthesis processes. Their solubility and stability make them suitable for formulation in various drug delivery systems, potentially leading to the development of novel treatments for metabolic disorders or neurological conditions.

In biochemical research, 3R-3-Hydroxy-L-aspartic acid hydrochloride serves as a tool for studying enzyme functions and metabolic pathways. Its role as an amino acid derivative allows researchers to investigate its involvement in enzyme-catalyzed reactions, contributing to a better understanding of metabolic processes. This research can be pivotal in identifying targets for drug development or understanding the basis of certain diseases. Its specificity and reactivity might also help elucidate mechanisms of action for other biochemical compounds.

The agricultural sector can also benefit from the applications of 3R-3-Hydroxy-L-aspartic acid hydrochloride. Amino acid derivatives are sometimes used to develop bio-stimulants for crops, aiming to enhance plant growth and resilience against environmental stress. These compounds can improve nutrient uptake in plants and promote healthier crop yields. Additionally, they can play a role in sustainable farming practices by reducing the reliance on synthetic chemicals and improving soil health through natural pathways.

In materials science, 3R-3-Hydroxy-L-aspartic acid hydrochloride might be used in the development of novel materials due to its unique chemical properties. Its functionality could contribute to the synthesis of polymers or coatings that are biocompatible or biodegradable, paving the way for advances in medical devices or environmentally friendly materials. Such applications leverage the inherent versatility of amino acid derivatives to achieve materials with specific characteristics, such as enhanced durability, flexibility, or reactivity.

1. Potent immunosuppressants, 2-alkyl-2-aminopropane-1,3-diols

T Fujita, R Hirose, M Yoneta, S Sasaki, K Inoue, M Kiuchi, S Hirase, K Chiba, H Sakamoto, M Arita J Med Chem. 1996 Oct 25;39(22):4451-9. doi: 10.1021/jm960391l.

Several immunosuppressants, ISP-I [(2S,3R,4R)-(E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoeicos++ +-6-enoic acid, myriocin = thermozymocidin] and mycestericins A-G, were isolated from culture broths of Isaria sinclairii and Mycelia sterilia, respectively. In order to investigate structure-activity relationships, extensive modifications of ISP-I were conducted, and it was established that the fundamental structure possessing the immunosuppressive activity is a symmetrical 2-alkyl-2-aminopropane-1,3-diol. The tetradecyl, pentadecyl, and hexadecyl derivatives prolonged rat skin allograft survival in the combination of LEW donor and F344 recipient and were more effective than cyclosporin A. Among them, 2-amino-2-tetradecylpropane-1,3-diol hydrochloride, ISP-I-55, showed the lowest toxicity. ISP-I-55 is a promising lead compound for the development of effective immunosuppressants for organ transplantations and for the treatment of autoimmune diseases.

2. Glutamate metabotropic receptors as targets for drug therapy in epilepsy

Randal X Moldrich, Astrid G Chapman, Giovambattista De Sarro, Brian S Meldrum Eur J Pharmacol. 2003 Aug 22;476(1-2):3-16. doi: 10.1016/s0014-2999(03)02149-6.

Metabotropic glutamate (mGlu) receptors have multiple actions on neuronal excitability through G-protein-linked modifications of enzymes and ion channels. They act presynaptically to modify glutamatergic and gamma-aminobutyric acid (GABA)-ergic transmission and can contribute to long-term changes in synaptic function. The recent identification of subtype-selective agonists and antagonists has permitted evaluation of mGlu receptors as potential targets in the treatment of epilepsy. Agonists acting on group I mGlu receptors (mGlu1 and mGlu5) are convulsant. Antagonists acting on mGlu1 or mGlu5 receptors are anticonvulsant against 3,5-dihydroxyphenylglycine (DHPG)-induced seizures and in mouse models of generalized motor seizures and absence seizures. The competitive, phenylglycine mGlu1/5 receptor antagonists generally require intracerebroventricular administration for potent anticonvulsant efficacy but noncompetitive antagonists, e.g., (3aS,6aS)-6a-naphthalen-2-ylmethyl-5-methyliden-hexahydrocyclopenta[c]furan-1-on (BAY36-7620), 2-methyl-6-(phenylethynyl)pyridine hydrochloride (MPEP), and 2-methyl-6-(2-phenylethenyl)pyridine (SIB-1893) block generalized seizures with systemic administration. Agonists acting on group II mGlu receptors (mGlu2, mGlu3) to reduce glutamate release are anticonvulsant, e.g., 2R,4R-aminopyrrolidine-2,4-dicarboxylate [(2R,4R)-APDC], (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740), and (-)-2-oxa-4-aminobicyclo[3.1.0]hexane-4,6-dicarboxylate (LY379268). The classical agonists acting on group III mGlu receptors such as L-(+)-2-amino-4-phosphonobutyric acid, and L-serine-O-phosphate are acutely proconvulsant with some anticonvulsant activity. The more recently identified agonists (R,S)-4-phosphonophenylglycine [(R,S)-PPG] and (S)-3,4-dicarboxyphenylglycine [(S)-3,4-DCPG] and (1S,3R,4S)-1-aminocyclopentane-1,2,4-tricarboxylic acid [ACPT-1] are all anticonvulsant without proconvulsant effects. Studies in animal models of kindling reveal some efficacy of mGlu receptor ligands against fully kindled limbic seizures. In genetic mouse models, mGlu1/5 antagonists and mGlu2/3 agonists are effective against absence seizures. Thus, antagonists at group I mGlu receptors and agonists at groups II and III mGlu receptors are potential antiepileptic agents, but their clinical usefulness will depend on their acute and chronic side effects. Potential also exists for combining mGlu receptor ligands with other glutamatergic and non-glutamatergic agents to produce an enhanced anticonvulsant effect. This review also discusses what is known about mGlu receptor expression and function in rodent epilepsy models and human epileptic conditions.

3. Discovery of 4-[4-({(3R)-1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic acid hydrochloride: a highly potent orally available CCR5 selective antagonist

Rena Nishizawa, et al. Bioorg Med Chem. 2011 Jul 1;19(13):4028-42. doi: 10.1016/j.bmc.2011.05.022. Epub 2011 May 20.

Based on the original spirodiketopiperazine design framework, further optimization of an orally available CCR5 antagonist was undertaken. Structural hybridization of the hydroxylated analog 4 derived from one of the oxidative metabolites and the new orally available non-hydroxylated benzoic acid analog 5 resulted in another potent orally available CCR5 antagonist 6a as a clinical candidate. Full details of a structure-activity relationship (SAR) study and ADME properties are presented.