l-Pipecolic acid - 3105-95-1

l-Pipecolic acid

Catalog Number: EVT-248208
CAS Number: 3105-95-1
Molecular Formula: C6H11NO2
Molecular Weight: 129.16 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
L-Pipecolic acid is a cyclic amino acid that is naturally found in plants, animals, and microorganisms. It is an important metabolite in the human body and plays a crucial role in various biological processes.
Applications in Various Fields
L-Pipecolic acid has various applications in medical, environmental, and industrial research. In medical research, it has been studied for its role in drug development and has been shown to have potential therapeutic effects in the treatment of neurological disorders. Clinical trials have also been conducted to investigate the safety and efficacy of l-Pipecolic acid in the treatment of various diseases. In environmental research, l-Pipecolic acid has been studied for its effects on ecosystems and its role in pollution management. It has also been investigated for its potential use in sustainable agriculture. In industrial research, l-Pipecolic acid has been used in manufacturing processes to improve product quality and efficiency. Health and safety considerations should be taken into account when using l-Pipecolic acid in industrial applications.

Properties

CAS Number

3105-95-1

Product Name

l-Pipecolic acid

IUPAC Name

(2S)-piperidine-2-carboxylic acid

Molecular Formula

C6H11NO2

Molecular Weight

129.16 g/mol

InChI

InChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)/t5-/m0/s1

InChI Key

HXEACLLIILLPRG-YFKPBYRVSA-N

SMILES

C1CCNC(C1)C(=O)O

Synonyms

l-Pipecolicacid;3105-95-1;(S)-Piperidine-2-carboxylicacid;L-Homoproline;L-Pipecolinicacid;(S)-(-)-2-Piperidinecarboxylicacid;(S)-pipecolicacid;L-pipecolate;l-piperidine-2-carboxylicacid;(l)-pipecolicacid;l(-)-pipecolinicacid;(2S)-piperidine-2-carboxylicacid;(-)-Pipecolicacid;l-homopro;(S)-2-Piperidinecarboxylicacid;L-Pipecolinate;h-homopro-oh;L-(-)-Pipecolinicacid;h-hopro-oh;(S)-(-)-pipecolicacid;(S)-Pipecolinate;(-)-Pipecolate;L-(-)-Pipecolate;(S)-Pipecolinicacid;(S)-pipecolate

Canonical SMILES

C1CC[NH2+]C(C1)C(=O)[O-]

Isomeric SMILES

C1CC[NH2+][C@@H](C1)C(=O)[O-]
Method of Synthesis or Extraction
L-Pipecolic acid can be synthesized by several methods, including chemical synthesis, microbial fermentation, and enzymatic synthesis. Chemical synthesis involves the reaction of 1,5-diaminopentane with acetic anhydride, followed by hydrolysis to obtain l-Pipecolic acid. Microbial fermentation involves the use of microorganisms such as Pseudomonas putida and Bacillus subtilis to produce l-Pipecolic acid from glucose or other carbon sources. Enzymatic synthesis involves the use of enzymes such as l-lysine 6-transaminase to convert l-lysine to l-Pipecolic acid. The efficiency and yield of each method vary, with microbial fermentation being the most efficient and yielding up to 80% of l-Pipecolic acid. Environmental and safety considerations should also be taken into account, as some methods may involve the use of toxic chemicals or generate hazardous waste.
Chemical Structure and Biological Activity
L-Pipecolic acid has a cyclic structure with a carboxylic acid group and an amino group. It is a non-proteinogenic amino acid and is not incorporated into proteins. l-Pipecolic acid is involved in various biological processes, including the biosynthesis of neurotransmitters, the regulation of immune responses, and the metabolism of fatty acids. It acts as a modulator of the GABAergic system and has been shown to have neuroprotective effects. It also plays a role in the regulation of the immune system and has been implicated in the pathogenesis of autoimmune diseases.
Biological Effects
L-Pipecolic acid has been shown to have various effects on cell function and signal transduction. It has been shown to modulate the activity of ion channels and receptors, including the GABA receptor and the NMDA receptor. It also affects the activity of enzymes involved in the metabolism of neurotransmitters and fatty acids. l-Pipecolic acid has potential therapeutic effects in the treatment of neurological disorders, such as epilepsy and Alzheimer's disease. However, it also has potential toxic effects, as high levels of l-Pipecolic acid have been associated with neurodegenerative diseases and autoimmune disorders.
Future Perspectives and Challenges
Despite the potential applications of l-Pipecolic acid, there are still limitations in its use and study. One of the challenges is the lack of understanding of its mechanisms of action and biological targets. Another challenge is the difficulty in synthesizing l-Pipecolic acid in large quantities. Possible solutions and improvements include the development of new methods for synthesizing l-Pipecolic acid and the identification of new biological targets. Future trends and prospects in the application of l-Pipecolic acid in scientific research include the development of new drugs for the treatment of neurological disorders and the investigation of its potential use in sustainable agriculture.

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