D-Nipecotic acid
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D-Nipecotic acid

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Category
Cyclic Amino Acids
Catalog number
BAT-006859
CAS number
25137-00-2
Molecular Formula
C6H11NO2
Molecular Weight
129.16
D-Nipecotic acid
IUPAC Name
(3R)-piperidine-3-carboxylic acid
Synonyms
H-D-Pic(3)-OH; H-D-Nipc-OH; (R)-Piperidine-3-carboxylic acid
Appearance
White crystalline solid
Purity
≥ 98% (assay by titration)
Density
1.125g/cm3
Melting Point
251-255 °C
Boiling Point
265.8°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C6H11NO2/c8-6(9)5-2-1-3-7-4-5/h5,7H,1-4H2,(H,8,9)/t5-/m1/s1
InChI Key
XJLSEXAGTJCILF-RXMQYKEDSA-N
Canonical SMILES
C1CC(CNC1)C(=O)O
1. The metabolism of D- and L-pipecolic acid in the rabbit and rat
J Dancis, J Hutzler Biochim Biophys Acta. 1981 Jul 17;675(3-4):411-5. doi: 10.1016/0304-4165(81)90034-9.
The metabolism of D- and L-pipecolic acid has been investigated in rabbits and rats. A rapid evolution of 14CO2 followed the injection of either D- or L-pipe[6-14C]colic acid into rabbits. Rabbit kidney slices degraded to CO2 both isomers of lysine and of pipecolic acid. Rabbit liver was effective with only the L-isomers. In the rat, very little of injected L-pipecolic acid was catabolized to CO2, and large amounts were excreted unchanged into the urine, L-Lysine was efficiently metabolized to CO2 by rat liver and kidney slices but not D-lysine or either isomer of pipecolic acid. Rat kidney converted D-lysine to L-pipecolic acid. The L-isomer was identified by co-precipitation of the radioactive product with authentic compounds.
2. Depression and anxiety in patients with active ulcerative colitis: crosstalk of gut microbiota, metabolomics and proteomics
Xiaomin Yuan, et al. Gut Microbes. 2021 Jan-Dec;13(1):1987779. doi: 10.1080/19490976.2021.1987779.
Patients with ulcerative colitis (UC) have a high prevalence of mental disorders, such as depression and anxiety. Gut microbiota imbalance and disturbed metabolism have been suggested to play an important role in either UC or mental disorders. However, little is known about their detailed multi-omics characteristics in patients with UC and depression/anxiety. In this prospective observational study, 240 Chinese patients were enrolled, including 129 patients with active UC (69 in Phase 1 and 60 in Phase 2; divided into depression/non-depression or anxiety/non-anxiety groups), 49 patients with depression and anxiety (non-UC), and 62 healthy people. The gut microbiota of all subjects was analyzed using 16S rRNA sequencing. The serum metabolome and proteome of patients with UC in Phase 2 were analyzed using liquid chromatography/mass spectrometry. Associations between multi-omics were evaluated by correlation analysis. The prophylactic effect of candidate metabolites on the depressive-like behavior of mice with colitis was investigated. In total, 58% of patients with active UC had depression, while 50% had anxiety. Compared to patients with UC without depression/anxiety, patients with UC and depression/anxiety had lower fecal microbial community richness and diversity, with more Lactobacillales, Sellimonas, Streptococcus, and Enterococcus but less Prevotella_9 and Lachnospira. Most metabolites (e.g., glycochenodeoxycholate) were increased in the serum, while few metabolites, including 2'-deoxy-D-ribose and L-pipecolic acid, were decreased, accompanied by a general reduction in immunoglobulin proteins. These related bacteria, metabolites, and proteins were highly connected. A prophylactic administration of 2'-deoxy-D-ribose and L-pipecolic acid significantly reduced the depressive-like behaviors in mice with colitis and alleviated the inflammatory cytokine levels in their colon, blood and brain. This study has identified a comprehensive multi-omics network related to depression and anxiety in active UC. It is composed of a certain set of gut microbiota, metabolites, and proteins, which are potential targets for clinical intervention for patients with UC and depression/anxiety.
3. Significance of the natural occurrence of L- versus D-pipecolic acid: a review
Valerie Vranova, Lea Lojkova, Klement Rejsek, Pavel Formanek Chirality. 2013 Dec;25(12):823-31. doi: 10.1002/chir.22237. Epub 2013 Sep 30.
Pipecolic acid naturally occurs in microorganisms, plants, and animals, where it plays many roles, including the interactions between these organisms, and is a key constituent of many natural and synthetic bioactive molecules. This article provides a review of current knowledge on the natural occurrence of pipecolic acid and the known and potential significance of its L- and D-enantiomers in different scientific disciplines. Knowledge gaps with perspectives for future research identified within this article include the roles of the L- versus the D-enantiomer of pipecolic acid in plant resistance, nutrient acquisition, and decontamination of polluted soils, as well as rhizosphere ecology and medical issues.
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