Chemical synthesis of N beta-oxalyl-L-alpha, beta-diaminopropionic acid and optical specificity in its neurotoxic action.

Biochemistry
S L Rao

Abstract

A practical procedure is described for the bulk synthesis of the neurotoxin N beta-oxalyl-L-alpha, beta-diaminopropionic acid (OA2pr3), a potential dicarboxylic amino acid antagonist of Lathyrus sativus seeds. L-Aspartic acid was reacted with sodium azide in 30% fuming sulfuric acid and L-alpha, beta-diaminopropionic acid hydrochloride (A2pr3-HCl) was isolated in yields greater than 75%. Potassium methyl oxalate was found to react selectively with the beta-amino group of S2pr3 resulting in near quantitative yields of OA2pr3. D-OA2pr3 has been made for the first time by this procedure. Unlike L-OA2pr3 the naturally occurring neurotoxin, D-OA2pr3, is not neuroactive even in high doses. The microsynthesis of L-[2,3-3H]A2pr3 from L-[2,3-3H]aspartic acid is also described, and the same procedure could also be used to prepare the neurotoxin with other labels. The availability of the neurotoxin in bulk and in labeled form should further experimental approaches to the understanding of its mechanism of action.

Citations

Jan 1, 1980·Toxicology and Applied Pharmacology·T MehtaB E Haskell
May 25, 2011·Chemical Communications : Chem Comm·Alvaro MallagarayJavier Pérez-Castells
Mar 17, 2009·Toxicon : Official Journal of the International Society on Toxinology·Peter B Nunn, Malarvizhi Ponnusamy
Sep 1, 1989·Journal of Neurochemistry·S M RossP S Spencer
May 30, 2006·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Jing ZhuZhangwan Li
Aug 12, 2005·Chemical Reviews·Alma VisoAida Flores

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.