Pyridoxin-d5

Katalognummer: B025862

CAS-Nummer: 688302-31-0

Molekulargewicht: 174.21 g/mol

InChI-Schlüssel: LXNHXLLTXMVWPM-WNWXXORZSA-N

Achtung: Nur für Forschungszwecke. Nicht für den menschlichen oder tierärztlichen Gebrauch.

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Übersicht

1. Beschreibung

7. Vergleich mit ähnlichen Verbindungen

2. Wissenschaftliche Forschungsanwendungen

8. Eigenschaften

3. Wirkmechanismus

9. Synthesis routes and methods I

4. Biochemische Analyse

10. Synthesis routes and methods II

5. Vorbereitungsmethoden

11. Retrosynthesis analysis

6. Analyse chemischer Reaktionen

12. Haftungsausschluss

Beschreibung

Pyridoxine-d5, also known as Pyridoxol-d5, is a deuterated form of Pyridoxine (Vitamin B6). It is a pyridine derivative and is chemically similar to natural Pyridoxine. The compound is labeled with deuterium, which is a stable isotope of hydrogen. Pyridoxine-d5 is primarily used in scientific research as a tracer in metabolic studies and for the investigation of biochemical pathways involving Vitamin B6.

Wissenschaftliche Forschungsanwendungen

Pyridoxine-d5 is widely used in scientific research due to its stable isotopic labeling. Some of its applications include:

Chemistry: Used as a tracer in metabolic studies to investigate the biochemical pathways of Vitamin B6.

Biology: Helps in studying the role of Vitamin B6 in cellular processes and enzyme functions.

Medicine: Used in pharmacokinetic studies to understand the metabolism and distribution of Vitamin B6 in the body.

Industry: Employed in the development of new drugs and therapeutic agents involving Vitamin B6.

Wirkmechanismus

Biochemische Analyse

Biochemical Properties

Pyridoxine-d5, like its non-deuterated form, is involved in a wide range of biochemical reactions. It interacts with various enzymes, proteins, and other biomolecules. The active endogenous metabolites of these molecules, pyridoxal phosphate and pyridoxamine phosphate, are the most important coenzymes involved in a wide range of biochemical reactions necessary for cell activity .

Cellular Effects

Pyridoxine-d5 has been shown to exert antioxidant effects in a cell model of Alzheimer’s disease via the Nrf-2/HO-1 pathway . In pancreatic acinar cells, pyridoxine availability can affect the gene expression profile .

Molecular Mechanism

The molecular mechanism of Pyridoxine-d5 involves its conversion to the active form, Pyridoxal 5’-phosphate (PLP), which is involved in many biochemical reactions, including the metabolism of amino acids and glycogen, the synthesis of nucleic acids, hemoglobin, sphingomyelin and other sphingolipids, and the synthesis of the neurotransmitters serotonin, dopamine .

Temporal Effects in Laboratory Settings

It is known that pyridoxine, the non-deuterated form, has a significant impact on post-prandial glucose levels when administered over a period of time .

Dosage Effects in Animal Models

In animal models, Pyridoxine-d5 has been shown to have a significant reduction to the postprandial glucose levels, when compared to the control. The maximum blood glucose levels of Pyridoxine-d5 administration group were decreased by about 18% and 19% in sucrose and starch loading tests, respectively .

Metabolic Pathways

Pyridoxine-d5 is involved in the Vitamin B6 metabolic pathway. This pathway involves the conversion of Pyridoxine-d5 to its active form, Pyridoxal 5’-phosphate (PLP), which is involved in a wide range of biochemical reactions .

Transport and Distribution

Pancreatic acinar cells obtain Pyridoxine-d5 from circulation, but little is known about the mechanism involved in the uptake process . After absorption, Pyridoxine-d5 is transported to the blood and other organs .

Subcellular Localization

It is known that the active form of Pyridoxine-d5, Pyridoxal 5’-phosphate (PLP), is involved in many biochemical reactions in various compartments of the cell .

Vorbereitungsmethoden

Synthetic Routes and Reaction Conditions

The synthesis of Pyridoxine-d5 involves the incorporation of deuterium into the Pyridoxine molecule. One common method is the catalytic hydrogenation of Pyridoxine in the presence of deuterium gas. This process replaces the hydrogen atoms in the molecule with deuterium atoms. The reaction typically occurs under mild conditions, using a palladium or platinum catalyst.

Industrial Production Methods

Industrial production of Pyridoxine-d5 follows similar synthetic routes but on a larger scale. The process involves the use of high-pressure reactors and specialized equipment to handle deuterium gas. The final product is purified through crystallization or chromatography to achieve the desired purity and isotopic labeling.

Analyse Chemischer Reaktionen

Types of Reactions

Pyridoxine-d5 undergoes various chemical reactions similar to those of natural Pyridoxine. These include:

Oxidation: Pyridoxine-d5 can be oxidized to Pyridoxal-d5, a form of Vitamin B6.

Reduction: Pyridoxal-d5 can be reduced back to Pyridoxine-d5.

Substitution: The hydroxyl group in Pyridoxine-d5 can be substituted with other functional groups.

Common Reagents and Conditions

Oxidation: Common oxidizing agents include potassium permanganate and hydrogen peroxide.

Reduction: Reducing agents such as sodium borohydride or lithium aluminum hydride are used.

Substitution: Various reagents like alkyl halides or acyl chlorides can be used for substitution reactions.

Major Products Formed

Oxidation: Pyridoxal-d5

Reduction: Pyridoxine-d5

Substitution: Various substituted Pyridoxine-d5 derivatives

Vergleich Mit ähnlichen Verbindungen

Pyridoxine-d5 is compared with other deuterated and non-deuterated forms of Vitamin B6, such as:

Pyridoxine: The natural form of Vitamin B6.

Pyridoxal: An oxidized form of Vitamin B6.

Pyridoxamine: Another form of Vitamin B6 involved in amino acid metabolism.

Uniqueness

The uniqueness of Pyridoxine-d5 lies in its deuterium labeling, which makes it an ideal tracer for metabolic studies. The presence of deuterium allows for precise tracking and analysis of biochemical pathways without altering the compound’s biological activity.

Conclusion

Pyridoxine-d5 is a valuable compound in scientific research, offering insights into the metabolic pathways and biochemical roles of Vitamin B6. Its stable isotopic labeling and similarity to natural Pyridoxine make it an essential tool in various fields, including chemistry, biology, medicine, and industry.

Eigenschaften

IUPAC Name	5-[dideuterio(hydroxy)methyl]-4-(hydroxymethyl)-2-(trideuteriomethyl)pyridin-3-ol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI	InChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3/i1D3,3D2	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI Key	LXNHXLLTXMVWPM-WNWXXORZSA-N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Canonical SMILES	CC1=NC=C(C(=C1O)CO)CO	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Isomeric SMILES	[2H]C([2H])([2H])C1=NC=C(C(=C1O)CO)C([2H])([2H])O	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C8H11NO3	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

DSSTOX Substance ID	DTXSID10574085	Source
Record name	4-(Hydroxymethyl)-5-[hydroxy(~2~H_2_)methyl]-2-(~2~H_3_)methylpyridin-3-ol
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID10574085
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Molecular Weight	174.21 g/mol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

CAS No.	688302-31-0	Source
Record name	4-(Hydroxymethyl)-5-[hydroxy(~2~H_2_)methyl]-2-(~2~H_3_)methylpyridin-3-ol
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID10574085
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Synthesis routes and methods I

Procedure details

In a second alternative and preferred workup, the reaction mixture (following complete conversion to compound (C)) is cooled to 20° C. and diluted with water (approximately 2.80 L of water for every 1 kg of starting pyridoxine HCl). After phase separation the organic phase is washed with water. The combined aqueous phases are reextracted twice with TBME. The combined TBME phases are washed once with saturated NaHCO3-solution and once with diluted brine. The MTBE-product solution is concentrated to a concentration of about 50% and stored at room temperature until it is further converted. If this second alternative workup is used, the volume of MTBE in the synthetic step is preferably reduced by about 26%.

[Compound]

Name

compound ( C )

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

pyridoxine HCl

Quantity

1 kg

Type

reactant

Reaction Step Two

Name

water

Quantity

0 (± 1) mol

Type

solvent

Reaction Step Two

Name

water

Quantity

2.8 L

Type

solvent

Reaction Step Two

Name

Pyridoxine

Details

Synthesis routes and methods II

Procedure details

In a similar manner as described in Example 3, S. meliloti PY-C341K1 was cultured in a flask containing LBMCG containing 10 μg/ml of Tc for 16 hours at 30° C., and the cell suspension of the strain was prepared. A tube containing 5 ml of the reaction mixtures composed of 0, 30, and 50 μg/ml of NTG and 1.6×109 cells per ml in 50 mM Tris-HCl buffer (pH 8.0) was incubated with a reciprocal shaking (275 rpm) for 30 min at 30° C. The cells of each reaction mixture were washed twice with sterile saline and suspended in saline. 100 μl of the cell suspension was spread onto agar plates containing LBMCG containing 10 μg/ml of Tc, and then the plates were incubated for 2-3 days at 30° C. The cells grown on the plates were recovered by suspending in sterile saline. After centrifugation of the suspension, the cell suspension was diluted to give a turbidity of OD600=1.6, and finally to 10−5. Each 100 μl of the diluents was spread onto five agar plates containing LBMCG containing 10 μg/ml of Tc and 0, 0.125, 0.15, or 0.175% glycine because 0.15% glycine completely inhibited the growth of S. meliloti PY-C341K1 on LBMCG plate, and then the plates were incubated for 4 days at 30° C. Ten colonies treated with 50 μg/ml of NTG grown on plates LBMCG containing 10 μg/ml of Tc and 0.175% glycine were picked up on LBMCG agar containing 10 μg/ml of Tc. After incubation for 2 days at 30° C., the productivity of vitamin B6 in ten colonies together with the parent strain (S. meliloti PY-C341K1) was examined by flask fermentation. One loopful cells was inoculated to tubes containing 8 ml of SM medium, and then the tubes were shaken on a reciprocal shaker (275 rpm) at 30° C. After shaking for 19 hours, each 4 ml of culture broth was transferred to a 500-ml flask with two baffles containing 200 ml of PM medium modified to 0.175% NH4Cl, and shaken on a rotary shaker (180 rpm) at 30° C. After shaking for 4 days, sterile solution of urea was added to the each flask at 0.125%, and the shaking were further continued for 3 days. The contents of vitamin B6 in the supernatant of 7-day culture broth were quantified by HPLC method as described in Example 3. As a result, S. meliloti PY-EGC1 produced 362 mg of pyridoxol per liter and was about 2.11 times higher than strain PY-341K1 (the parent).

[Compound]

Name

reaction

Quantity

5 mL

Type

reactant

Reaction Step One

Name

glycine

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

glycine

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

glycine

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Three

Name

vitamin B6

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Four

Name

NH4Cl

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Five

Name

urea

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Six

Name

vitamin B6

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Seven

Name

Tris-HCl

Quantity

0 (± 1) mol

Type

solvent

Reaction Step Eight

Name

pyridoxol

Details

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

One-Step Synthesis Focus: Specifically designed for one-step synthesis, it provides concise and direct routes for your target compounds, streamlining the synthesis process.

Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.

Strategy Settings

Precursor scoring	Relevance Heuristic
Min. plausibility	0.01
Model	Template_relevance
Template Set	Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph	6

Feasible Synthetic Routes

Reactant of Route 1

Pyridoxine-d5

Reactant of Route 2

Pyridoxine-d5

Reactant of Route 3

Pyridoxine-d5

Reactant of Route 4

Pyridoxine-d5

Reactant of Route 5

Pyridoxine-d5

Reactant of Route 6

Pyridoxine-d5

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