54-47-7

Basic information

• Product Name: Pyridoxal phosphate
• Synonyms: PYRIDOXAL-5-PHOSPHORIC ACID;PYRIDOXAL 5'-MONOPHOSPHATE;CODECARBOXYLASE;3-hydroxy-2-methyl-5-((phosphonooxy)methyl)-4-pyridinecarboxaldehyd;3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyd;apolonb(sub6);apolonb6;biosechs
• CAS NO: 54-47-7
• Molecular Formula: C₈H₁₀NO₆P
• Molecular Weight: 247.14
• EINECS: 200-208-3
• Product Categories: Vitamins and derivatives;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Phosphorylating and Phosphitylating Agents
• Mol File: 54-47-7.mol

Chemical Properties

• Melting Point: 140-143 °C
• Boiling Point: 565.746 °C at 760 mmHg
• Flash Point: 295.952 °C
• Appearance: /powder
• Density: 1.638 g/cm³
• Storage Temp.: −20°C
• PKA: 1.56±0.10(Predicted)
• CAS DataBase Reference: Pyridoxal phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridoxal phosphate(54-47-7)
• EPA Substance Registry System: Pyridoxal phosphate(54-47-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 8-10-23
• Hazardous Substances Data: 54-47-7(Hazardous Substances Data)

Usage

Uses

Used in the Pharmaceutical Industry:
Pyridoxal phosphate is used as an enzyme co-factor for facilitating various biochemical reactions in the body, such as transamination, α-decarboxylation, β-decarboxylation, β-elimination, γ-elimination, racemization, and aldol reactions. These reactions are essential for the proper functioning of the human body and maintaining overall health.
Used in the Nutritional Supplement Industry:
Pyridoxal phosphate is used as a key component in vitamin B6 supplements, which are crucial for various physiological processes, including the synthesis of neurotransmitters, hemoglobin, and immune system support. It also plays a role in converting tryptophan to niacin and is involved in the metabolism of lipids and carbohydrates.
Used in the Food Industry:
Pyridoxal phosphate is utilized as an additive in the food industry to enhance the nutritional value of certain products, particularly those fortified with vitamin B6. It helps maintain the proper balance of essential nutrients in the human diet.
Used in the Cosmetic Industry:
Pyridoxal phosphate is also used in the cosmetic industry for its skin-friendly properties. It is often included in skincare products to promote healthy skin and hair, as it plays a role in the synthesis of amino acids, which are the building blocks of proteins in the skin and hair.

Biological Functions

Pyridoxal phosphate is the coenzyme form of vitamin B6. In the catalytic reaction, the intramolecular aldehyde group of pyridoxal phosphate is combined with the amino group of α-amino acid to form an aldimine, also known as Schiffbase, and then the amino acid undergoes transamination, decarboxylation or racemization according to the characteristics of different enzymes and proteins. . As a coenzyme of amino acid transaminase, decarboxylase and racemase, it plays a very important role in amino acid metabolism.

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 4693, 1951 DOI: 10.1021/ja01154a062

Purification Methods

PLP has been purified by dissolving 2g in H2O (10-15mL, in a dialysis bag a third full) and dialysing with gentle stirring against 1L of H2O (+ two drops of toluene) for 15hours in a cold room. The dialysate is evaporated to 80-100mL, then lyophilised. Lemon yellow microscopic needles of the monohydrate remain when all the ice crystals have been removed. The purity is checked by paper chromatography (in EtOH or n-PrOH/NH3) and the spot(s) visualised under UV light after reaction with a spray of p-phenylene diamine, NH3 and molybdate. Solutions stored in a freezer are 2-3% hydrolysed in 3weeks. At 25o, only 4-6% hydrolysis occurs even in N NaOH or HCl, and 2% is hydrolysed at 37o in 1day-but is complete at 100o in 4hours. It is best stored as a dry solid at -20o. In aqueous acid the solution is colourless but is yellow in alkaline solutions. It has UV max at 305nm ( 1100) and 380nm ( 6550) in 0.1 N NaOH; 330nm ( 2450) and 388nm ( 4,900) in 0.05M phosphate buffer pH 7.0 and 295nm ( 6700) in 0.1N HCl. [Peterson et al. Biochemical Preparations 3 34, 119 1953.] The oxime decomposes at 229-230o and is practically insoluble in H2O, EtOH and Et2O. The O-methyloxime decomposes at 212-213o. [Heyl et al. J Am Chem Soc 73 3430 1951.] It has also been purified by column chromatography through Amberlite IRC-50 (H+) [Peterson & Sober J Am Chem Soc 76 169 1954]. [Beilstein 21/13 V 46.]

Synthetic route

pyridoxal hydrochloride (65-22-5) → pyridoxal 5'-phosphate (54-47-7)

Conditions	Yield
Stage #1: pyridoxal hydrochloride With N,N-dimethylethylenediamine In 5,5-dimethyl-1,3-cyclohexadiene at 90℃; for 8h; Stage #2: With polyphosphoric acid at 70℃; for 12h; Solvent;	76%
With water; trichlorophosphate In tetrahydrofuran at 0 - 20℃; for 5h; Reagent/catalyst; Solvent; Temperature;

Phosphoric acid mono-(4-{[(Z)-4-ethoxy-phenylimino]-methyl}-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester (15847-87-7) → pyridoxal 5'-phosphate (54-47-7)

Conditions	Yield
With sodium hydroxide at 35℃; for 2h;	68.4%

pyridoxamine-5'-phosphate (529-96-4) → pyridoxal 5'-phosphate (54-47-7)

Conditions	Yield
With manganese(IV) oxide; Celite in schwach saurer wss.Loesung;
With manganese(IV) oxide; sulfuric acid; water at 70℃;
With copper(II) sulfate; 2-oxo-propionic acid in wss.Loesung;
With copper diacetate; 2-oxo-propionic acid in wss.Loesung;

5-hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridylmethyl dihydrogen phosphate (447-05-2) → pyridoxal 5'-phosphate (54-47-7)

Conditions	Yield
With manganese(IV) oxide; sulfuric acid; water at 70℃;

pyridoxal (66-72-8) → pyridoxal 5'-phosphate (54-47-7)

Conditions	Yield
With water; trichlorophosphate

triphosphoric acid-1-(4-{[(N,N-dimethyl-glycyl)-hydrazono]-methyl}-5-hydroxy-6-methyl-[3]pyridylmethyl ester) → pyridoxal 5'-phosphate (54-47-7)

Conditions	Yield
With hydrogenchloride; silver(I) nitrite; water at 100℃;

pyridoxalphosphate (1499-44-1) → pyridoxal 5'-phosphate (54-47-7) + glycine (56-40-6)

Conditions	Yield
In water at 25℃; Equilibrium constant; Mechanism; over a wide pH range;
at 19.99℃; pH=7.35; Equilibrium constant; aq. phosphate buffer;

C14H23N2O5P (10524-83-1) → hexan-1-amine (111-26-2) + pyridoxal 5'-phosphate (54-47-7)

Conditions	Yield
With water at 25℃; Rate constant; also in var. H2O-dioxane solutions; var. pH's;

6-{[1-(3-Hydroxy-2-methyl-5-phosphonooxymethyl-pyridin-4-yl)-meth-(Z)-ylidene]-amino}-hexanoic acid (96594-16-0) → pyridoxal 5'-phosphate (54-47-7) + 6-aminohexanoic acid (60-32-2)

Conditions	Yield
In water at 25℃; Equilibrium constant; Mechanism; over a wide pH range;

2-{[1-(3-Hydroxy-2-methyl-5-phosphonooxymethyl-pyridin-4-yl)-meth-(Z)-ylidene]-amino}-4-methyl-pentanoic acid (133156-44-2) → L-leucine (61-90-5) + pyridoxal 5'-phosphate (54-47-7)

Conditions	Yield
In water at 25℃; Equilibrium constant; Mechanism; over a wide pH range;

(2S,3S)-2-{[1-(3-Hydroxy-2-methyl-5-phosphonooxymethyl-pyridin-4-yl)-meth-(Z)-ylidene]-amino}-3-methyl-pentanoic acid (80995-96-6) → L-isoleucine (73-32-5) + pyridoxal 5'-phosphate (54-47-7)

Conditions	Yield
In water at 25℃; Equilibrium constant; Mechanism; over a wide pH range;
With phosphate buffer; Carbonate buffer at 25℃; Equilibrium constant; var. pH;

Phosphoric acid mono-{4-[(Z)-hexyliminomethyl]-5-hydroxy-6-methyl-pyridin-3-ylmethyl} ester (10524-83-1) → hexan-1-amine (111-26-2) + pyridoxal 5'-phosphate (54-47-7)

Conditions	Yield
With pH = 3.6, I = 0.1 In water at 25℃; Equilibrium constant;

(S)-2-{[1-(3-Hydroxy-2-methyl-5-phosphonooxymethyl-pyridin-4-yl)-meth-(Z)-ylidene]-amino}-4-methyl-pentanoic acid (133156-44-2) → L-leucine (61-90-5) + pyridoxal 5'-phosphate (54-47-7)

Conditions	Yield
With water Rate constant; Equilibrium constant; dependence on pH, also in the presence of cetyltrimethylammonium bromide;
With phosphate buffer; Carbonate buffer at 25℃; Equilibrium constant; var. pH;

Phosphoric acid mono-(4-{[(Z)-(S)-1-dodecylcarbamoyl-ethylimino]-methyl}-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester (83825-03-0) → pyridoxal 5'-phosphate (54-47-7) + N-Dodecyl-(S)-alaninamide (110139-25-8)

Conditions	Yield
With phosphate buffer; ethanol; potassium chloride In 1,4-dioxane; water at 30℃; Equilibrium constant; also in the presence of CTAB, N,N-ditetradecyl-Nα-(6-trimethylammoniohexanoyl)-L-histidinamide bromide and N,N-ditetradecyl-Nα-(6-trimethyammoniohexanoyl)-L-alaninamide bromide;

(S)-2-{[1-(3-Hydroxy-2-methyl-5-phosphonooxymethyl-pyridin-4-yl)-meth-(E)-ylidene]-amino}-propionic acid → L-alanin (56-41-7) + pyridoxal 5'-phosphate (54-47-7)

Conditions	Yield
With phosphate buffer; Carbonate buffer at 25℃; Equilibrium constant; var. pH;
at 19.99℃; pH=7.35; Equilibrium constant; aq. phosphate buffer;

{3-hydroxy-4-[(E)-(isonicotinoylhydrazono)methyl]-2-methylpyridin-5-yl}methylphosphate (53-91-8) → isoniazid (54-85-3) + pyridoxal 5'-phosphate (54-47-7)

Conditions	Yield
at 25℃; Equilibrium constant; Rate constant; depending on pH;

Phosphoric acid mono-[5-hydroxy-6-methyl-4-(phthalazin-1-yl-hydrazonomethyl)-pyridin-3-ylmethyl] ester → 1-hydrazinophthalazine (1044569-46-1) + pyridoxal 5'-phosphate (54-47-7)

Conditions	Yield
at 25℃; Equilibrium constant; Rate constant; depending on pH;

(S)-3-(3,4-Dihydroxy-phenyl)-2-{N'-[1-(3-hydroxy-2-methyl-5-phosphonooxymethyl-pyridin-4-yl)-meth-(E)-ylidene]-hydrazino}-2-methyl-propionic acid → pyridoxal 5'-phosphate (54-47-7) + S(-)-carbidopa (302-53-4, 14585-65-0, 28860-95-9, 28875-92-5)

Conditions	Yield
at 25℃; Equilibrium constant; Rate constant; depending on pH;

(E)-N'-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)benzohydrazide (72343-06-7) + metaphosphoric acid → pyridoxal 5'-phosphate (54-47-7)

Conditions	Yield
at 60℃; und Erwaermen des Reaktionsprodukts mit wss.Salzsaeure und Silbernitrit auf 100grad;

D-Fructose (57-48-7) + L-leucine (61-90-5) → pyridoxamine-5'-phosphate (529-96-4) + pyridoxal 5'-phosphate (54-47-7) + pyridoxal (66-72-8) + pyridoxamine (85-87-0)

Conditions	Yield
With air; ATCC 38399 h- leu1-32 In various solvent(s) at 30℃; for 36h; pH=4.5; Product distribution; Further Variations:; Reagents; reaction times; Microbiological reaction;

D-Glucose (2280-44-6) + L-leucine (61-90-5) → pyridoxamine-5'-phosphate (529-96-4) + pyridoxal 5'-phosphate (54-47-7) + pyridoxal (66-72-8) + pyridoxamine (85-87-0)

Conditions	Yield
With air; ATCC 38399 h- leu1-32 In various solvent(s) at 30℃; for 36h; pH=4.5; Product distribution; Further Variations:; Reagents; reaction times; Microbiological reaction;

Maltose (133-99-3, 490-37-9, 2152-98-9, 4482-75-1, 5965-66-2, 13299-27-9, 13360-52-6, 14641-93-1, 15548-43-3, 16462-44-5, 16984-36-4, 16984-38-6, 20869-27-6, 22688-72-8, 27452-49-9, 29276-55-9, 30608-12-9, 34481-13-5, 37169-60-1, 37169-64-5, 64234-01-1, 64234-02-2, 75281-88-8, 80446-85-1, 84413-57-0, 92344-56-4, 93221-87-5, 93301-77-0, 94799-29-8, 100427-98-3, 100428-00-0, 101312-82-7, 102046-24-2, 102046-25-3, 109432-00-0, 109432-02-2, 109432-04-4, 109432-08-8, 135268-49-4, 138231-26-2, 140461-59-2, 145414-22-8, 145414-26-2, 146339-75-5, 146339-76-6, 149116-55-2, 6363-53-7) + L-leucine (61-90-5) → pyridoxamine-5'-phosphate (529-96-4) + pyridoxal 5'-phosphate (54-47-7) + pyridoxal (66-72-8) + pyridoxamine (85-87-0)

Conditions	Yield
With air; ATCC 38399 h- leu1-32 In various solvent(s) at 30℃; for 36h; pH=4.5; Product distribution; Further Variations:; Reagents; reaction times; Microbiological reaction;

D-Mannose (3458-28-4) + L-leucine (61-90-5) → pyridoxamine-5'-phosphate (529-96-4) + pyridoxal 5'-phosphate (54-47-7) + pyridoxal (66-72-8) + pyridoxamine (85-87-0)

Conditions	Yield
With air; ATCC 38399 h- leu1-32 In various solvent(s) at 30℃; for 36h; pH=4.5; Product distribution; Further Variations:; Reagents; reaction times; Microbiological reaction;

L-leucine (61-90-5) + Sucrose (57-50-1) → pyridoxamine-5'-phosphate (529-96-4) + pyridoxal 5'-phosphate (54-47-7) + pyridoxal (66-72-8) + pyridoxamine (85-87-0)

Conditions	Yield
With air; ATCC 38399 h- leu1-32 In various solvent(s) at 30℃; for 36h; pH=4.5; Product distribution; Further Variations:; Reagents; reaction times; Microbiological reaction;

N-(3-hydroxy-2-methyl-5-phosphonooxymethyl-[4]pyridylmethylen)-alanine (98969-65-4) → pyridoxal 5'-phosphate (54-47-7) + rac-Ala-OH (302-72-7)

Conditions	Yield
With potassium chloride; potassium acetate at 25℃; pH=5; Equilibrium constant; Further Variations:; pH-values;

pyridoxal phosphate adduct of ethylamine → pyridoxal 5'-phosphate (54-47-7) + ethylamine (75-04-7)

Conditions	Yield
With potassium chloride; potassium acetate at 25℃; pH=5; Equilibrium constant;

2-{[1-(3-Hydroxy-2-methyl-5-phosphonooxymethyl-pyridin-4-yl)-meth-(E)-ylidene]-amino}-2-methyl-propionic acid → pyridoxal 5'-phosphate (54-47-7) + 2-Aminoisobutyric acid (62-57-7)

Conditions	Yield
With potassium chloride; potassium acetate at 25℃; pH=5; Equilibrium constant; Further Variations:; pH-values;

2-{[1-(3-Hydroxy-2-methyl-5-phosphonooxymethyl-pyridin-4-yl)-meth-(E)-ylidene]-amino}-2-methyl-malonic acid → α-amino-α-methylmalonic acid (26767-88-4) + pyridoxal 5'-phosphate (54-47-7)

Conditions	Yield
With potassium chloride; potassium acetate at 25℃; pH=5; Equilibrium constant;

(S)-3-(3,4-Dihydroxy-phenyl)-2-{[1-(3-hydroxy-2-methyl-5-phosphonooxymethyl-pyridin-4-yl)-meth-(E)-ylidene]-amino}-propionic acid → levodopa (59-92-7) + pyridoxal 5'-phosphate (54-47-7)

Conditions	Yield
In water at 25℃; pH=7; Kinetics; Further Variations:; pH-values;

pyridoxal 5'-phosphate (54-47-7) + 3-(aminooxy)-2-fluoropropanamine dihydrochloride (130545-04-9, 139526-94-6) → 2-fluoro-3-<<<<3-hydroxy-2-methyl-5-<(phosphonooxy)methyl>-4-pyridyl>methylidene>amino>oxy>propanamine hydrochloride (130545-69-6, 139527-03-0)

Conditions	Yield
With sodium hydroxide for 1h; Ambient temperature;	99%

pyridoxal 5'-phosphate (54-47-7) + 3,5-Dichloroaniline (626-43-7) → C14H13Cl2N2O5P

Conditions	Yield
In methanol at 20℃; for 24h;	98%

pyridoxal 5'-phosphate (54-47-7) + 2,6-dimethylaniline (87-62-7) → C16H19N2O5P

Conditions	Yield
In methanol at 20℃; for 24h;	98%

pyridoxal 5'-phosphate (54-47-7) + 4-nitro-aniline (100-01-6) → C14H14N3O7P

Conditions	Yield
In methanol at 20℃; for 24h;	96%

pyridoxal 5'-phosphate (54-47-7) + diethyltin(IV) oxide (3682-12-0) → Sn(4+)*2CH3CH2(1-)*CH3C5HNH(O)(CHO)CH2OPO3(2-)*0.5H2O=[Sn(CH2CH3)2(CH3C5HN(OH)(CHO)CH2OPO3)]*0.5H2O

Conditions	Yield
In ethanol; toluene Et2SnO added to soln. of pyridoxal 5-phosphate, refluxed for 10 h; distn., filtration, vac. drying, elem. anal.;	95%

pyridoxal 5'-phosphate (54-47-7) + di(n-butyl)tin oxide (818-08-6) → Sn(4+)*2CH3(CH2)3(1-)*CH3C5HNH(O)(CHO)CH2OPO3(2-)=[Sn((CH2)3CH3)2(CH3C5HN(OH)(CHO)CH2OPO3)]

Conditions	Yield
In ethanol; toluene Bu2SnO added to soln. of pyridoxal 5-phosphate, refluxed for 10 h; distn., filtration, vac. drying, elem. anal.;	95%

pyridoxal 5'-phosphate (54-47-7) + dimethyltin oxide (2273-45-2) → Sn(4+)*2CH3(1-)*CH3C5HNH(O)(CHO)CH2OPO3(2-)=[Sn(CH3)2(CH3C5HN(OH)(CHO)CH2OPO3)]

Conditions	Yield
In ethanol; toluene (CH3)2SnO added to soln. of pyridoxal 5-phosphate, refluxed for 10 h; distn., filtration, vac. drying, elem. anal.;	95%

pyridoxal 5'-phosphate (54-47-7) + 4-chloro-aniline (106-47-8) → Phosphoric acid mono-(4-{[(Z)-4-chloro-phenylimino]-methyl}-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester (5371-85-7)

Conditions	Yield
In methanol at 20℃; for 24h;	93%

pyridoxal 5'-phosphate (54-47-7) + 4-methoxy-aniline (104-94-9) → C15H17N2O6P

Conditions	Yield
In methanol at 20℃; for 24h;	92%

pyridoxal 5'-phosphate (54-47-7) + 1-amino-3-(aminooxy)-2-propanol dihydrochloride (67435-03-4, 130545-48-1, 139526-70-8, 139526-72-0, 139627-59-1) → C11H18N3O7P*2ClH*ClNa (130545-70-9, 139527-01-8)

Conditions	Yield
With sodium hydroxide for 1h; Ambient temperature;	91%

dimethyltin-diacetate + pyridoxal 5'-phosphate (54-47-7) + water (7732-18-5) → Sn(4+)*2CH3(1-)*CH3C5HNH(O)(CHO)CH2OPO3(2-)*1.5H2O=[Sn(CH3)2(CH3C5HN(OH)(CHO)CH2OPO3)]*1.5H2O

Conditions	Yield
With valine In methanol; water valine added to pyridoxal 5-phosphate in methanol-water (3:1), SnMe2(OAc)2 added and stirred for 12 h; filtration, washing (abs. methanol), vac. drying, elem. anal.;	89%

pyridoxal 5'-phosphate (54-47-7) + 2,4-Xylidine (95-68-1) → C16H19N2O5P

Conditions	Yield
In methanol at 20℃; for 24h;	89%

pyridoxal 5'-phosphate (54-47-7) + naphthalen-2-ylamine (91-59-8) → (5-hydroxy-6-methyl-4-[(naphthalen-2-ylimino)methyl]pyridin-3-yl)methyl dihydrogen phosphate

Conditions	Yield
In methanol at 20℃; for 24h;	88.5%

pyridoxal 5'-phosphate (54-47-7) + L-Tryptophan (73-22-3) → 3-carboxy-1-<3-hydroxy-2-methyl-5-<(phosphonooxy)methyl>-4-pyridyl>-1,2,3,4-tetrahydro-β-carboline

Conditions	Yield
With potassium phosphate buffer at 37℃;	88.2%
In water at 50 - 55℃; for 1h;

2-thioxo-4-thiazolidinone (141-84-4) + pyridoxal 5'-phosphate (54-47-7) → (Z)-5'-O-phosphono-pyridoxylidenerhodanine

Conditions	Yield
In ethanol for 0.333333h; Heating;	88%
In ethanol Heating;	85%

3-(piperidine-1-sulfonyl)-phenylamine (22184-99-2) + pyridoxal 5'-phosphate (54-47-7) → 6-[3-(1-Piperidinesulfonyl)phenylazo]-pyridoxal-5-phosphate (608523-46-2)

Conditions	Yield
	88%

pyridoxal 5'-phosphate (54-47-7) + 6'-amino-3,6-dihydroxyspiro-3'-one (51649-83-3) → C28H21N2O10P

Conditions	Yield
In ethanol for 4h; Reflux;	88%

pyridoxal 5'-phosphate (54-47-7) + aniline (62-53-3) → (5-hydroxy-6-methyl-4-[(phenylimino)methyl]pyridin-3-yl)methyl dihydrogen phosphate (5371-86-8)

Conditions	Yield
In methanol at 20℃; for 24h;	88%
In methanol at 24.84℃;	70%
In methanol for 48h;	44%

pyridoxal 5'-phosphate (54-47-7) + L-Lysine hydrochloride (657-27-2, 10098-89-2) → ε-(5-phosphopyridoxinyl)-L-lysine + α,ε-bis(5-phosphopyridoxinyl)-L-lysine

Conditions	Yield
With potassium hydroxide; sodium tetrahydroborate In methanol at -15℃; for 1h;	A 87% B n/a

meta-fluoroaniline (372-19-0) + pyridoxal 5'-phosphate (54-47-7) → 6-(3-fluorophenylazo)pyridoxal-5'-phosphate

Conditions	Yield
Stage #1: meta-fluoroaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.0833333h; diazotization; Stage #2: pyridoxal 5'-phosphate With sodium hydroxide In water at 0℃; for 0.5h; pH=9; substitution;	87%

rhodamine hydrazide (932013-08-6) + pyridoxal 5'-phosphate (54-47-7) → C34H36N5O7P

Conditions	Yield
With acetic acid In methanol for 4h; Reflux;	87%

4-Fluoro-3-nitroaniline (364-76-1) + pyridoxal 5'-phosphate (54-47-7) → 6-(4-fluoro-3-nitrophenylazo)pyridoxal-5'-phosphate

Conditions	Yield
Stage #1: 4-Fluoro-3-nitroaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.0833333h; diazotization; Stage #2: pyridoxal 5'-phosphate With sodium hydroxide In water at 0℃; for 0.5h; pH=9; substitution;	86%

1-(2-aminoethyl)-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic acid tri(1,1-dimethylethyl ester) (824984-75-0) + pyridoxal 5'-phosphate (54-47-7) → 1,4,7-tris(tert-butoxycarbonylmethyl)-10-{2-[(3-hydroxy-2-methyl-5-phosphonooxy-methyl-pyridin-4-ylmethylene)-amino]-ethyl}-1,4,7,10-tetraazacyclododecane (879999-83-4)

Conditions	Yield
In methanol at 4 - 25℃; for 4h;	85%

pyridoxal 5'-phosphate (54-47-7) + 3-amino-2-methylbenzoic acid (52130-17-3) → 6-(3-Carboxy-2-methylphenylazo)-pyridoxal-5-phosphate (608523-41-7)

Conditions	Yield
	85%

pyridoxal 5'-phosphate (54-47-7) + 2-amino-benzenethiol (137-07-5) → C14H15N2O5PS

Conditions	Yield
In methanol	85%

pyridoxal 5'-phosphate (54-47-7) + 2-(3,5-dimethyl-1H-pyrazol-4-yl)acetohydrazide → {4-[(Z)-{[(3,5-dimethyl-1H-pyrazol-4-yl)acetyl]-hydrazono}methyl]-3-hydroxy-2-methylpyridin-5-yl}methyl phosphate

Conditions	Yield
In water at 50℃; pH=7.44; Kinetics; pH-value;	85%

pyridoxal 5'-phosphate (54-47-7) + 3-methyl-1H-pyrazole-5-carbohydrazide (40535-14-6) → {3-hydroxy-2-methyl-4-[(Z)-{[(5-methyl-1H-pyrazol-3-yl)carbonyl]hydrazono}methyl]pyridin-5-yl}methyl phosphate

Conditions	Yield
In water at 50℃; pH=7.44; Kinetics; pH-value;	85%

pyridoxal 5'-phosphate (54-47-7) + 1H-pyrazole-3-carbohydrazide (26275-64-9) → (3-hydroxy-2-methyl-4-{(Z)-[(1H-pyrazol-3-ylcarbonyl)hydrazono]methyl}pyridin-5-yl)methyl phosphate

Conditions	Yield
In water at 50℃;	85%

pyrazine-2-carbohydrazide (768-05-8) + pyridoxal 5'-phosphate (54-47-7) → (5-hydroxy-6-methyl-4-{(E)-[2-oxo-2-(pyrazin-2-yl)ethyl]hydrazinylidenemethyl}pyridin-3-yl)methylphosphate

Conditions	Yield
In water at 20 - 80℃; for 1h;	84.6%

pyridoxal 5'-phosphate (54-47-7) + N-adamantan-1-yl-4-aminobenzenesulfonamide (24224-95-1) → 6-[4-(N-(1-Adamantyl)sulfamoyl)phenylazo]-pyridoxal-5-phosphate Hydrochloride

Conditions	Yield
	84%

Upstream product

• 447-05-2 5-hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridylmethyl dihydrogen phosphate 
• 2280-44-6 D-Glucose 
• 61-90-5 L-leucine 
• 80995-96-6 (2S,3S)-2-{[1-(3-Hydroxy-2-methyl-5-phosphonooxymethyl-pyridin-4-yl)-meth-(Z)-ylidene]-amino}-3-methyl-pentanoic acid 
• 133156-44-2 2-{[1-(3-Hydroxy-2-methyl-5-phosphonooxymethyl-pyridin-4-yl)-meth-(Z)-ylidene]-amino}-4-methyl-pentanoic acid 
• 10524-83-1 C₁₄H₂₃N₂O₅P 
• 66-72-8 pyridoxal 
• 529-96-4 pyridoxamine-5'-phosphate 
• 15847-87-7 Phosphoric acid mono-(4-{[(Z)-4-ethoxy-phenylimino]-methyl}-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester 
• 76532-72-4 C₁₄H₂₂N₃O₇P 
• 17280-36-3 C₁₂H₁₅N₂O₉P 
• 21888-14-2 C₁₃H₁₇N₂O₉P 

Downstream Products

• 529-96-4 pyridoxamine-5'-phosphate 
• 75-07-0 acetaldehyde 
• 127-17-3 2-oxo-propionic acid 
• 608523-74-6 6-(3-Chlorophenylazo)-pyridoxal-5-phosphate 
• 608523-79-1 6-(3-Carboxy-2-chlorophenylazo)-pyridoxal-5-phosphate 

Relevant articles and documents

Preparation method of pyridoxal 5-phosphate monohydrate

The invention provides a preparation method of pyridoxal 5-phosphate monohydrate. The preparation method comprises the following steps: 1, first oxidizing pyridoxine hydrochloride to pyridoxal hydrochloride, adding sodium sulfide, then dropwise adding p-ethoxyaniline to the solution, and carrying out a reaction to produce a pyridoxal hydrochloride Schiff base; 2, adding polyphosphoric acid to thepyridoxal hydrochloride Schiff base, performing a stirring reaction, first hydrolyzing polyphosphoric acid and then performing neutralization with an alkali solution to precipitate a large amount of an orange-red solid after the reaction is completed, and filtering and washing the solid to obtain a pyridoxal 5-phosphate Schiff base; and 3, hydrolyzing the pyridoxal 5-phosphate Schiff base with a 2mol/L of alkali solution, adding an organic solvent for extracting and performing liquid separation, adding a strong acid cation exchange resin into the aqueous phase, performing stirring for 1.0 h and then performing vacuum filtration, and performing freeze drying on the filtrate to obtain pyridoxal 5-phosphate monohydrate. The preparation method of pyridoxal 5-phosphate monohydrate is simple inoperation, mild in reaction conditions, relatively high in purity and yield of the final product, and suitable for industrial application, and has relatively good economic benefits.

Thermodynamics and Kinetics of the Reaction between Pyridoxal-5-Phosphate and Hydrazides of 2-Methylfuran-3-Carboxylic and Thiophene-3-Carboxylic Acids in an Aqueous Solution

Abstract: The stability constants of pyridoxal-5-phosphate hydrazones formed with 2-methylfuran-3-carbohydrazide and thiophene-3-carbohydrazide in an aqueous solution at pH 1.9, 6.6, 7.0, and 7.4 are determined via spectrophotometry. The kinetics of the processes of formation and hydrolysis of the Schiff bases are studied, and the constant of the direct and reverse reactions are calculated from the electronic absorption spectra. The stability constants of the Schiff bases are calculated from their ratio. The thermodynamic parameters of the reaction of formation (log K, ΔH, and TΔS) of both hydrazones at pH 6.6 are determined via calorimetry. The reasons for the differences between the equilibrium constants calculated from the data of spectrophotometric and kinetic experiments are discussed, and the reliability of the obtained results is analyzed.

Synthesis method of pyridoxal phosphate

The invention relates to the technical field of chemical synthesis, and concretely discloses a synthesis method of pyridoxal phosphate. The synthesis method of pyridoxal phosphate comprises the following steps: carrying out an oxidation reaction on pyridoxol hydrochloride under the action of active manganese dioxide to prepare pyridoxal hydrochloride; carrying out a condensation reaction on the pyridoxal hydrochloride and N,N-dimethylethylenediamine to obtain a pyridoxal condensate; and carrying out a phosphate esterification reaction on the pyridoxal condensate under the action of polyphosphoric acid to obtain crude pyridoxal phosphate, and purifying and crystallizing the crude pyridoxal phosphate to obtain the pyridoxal phosphate product. The method has the advantages of easily availableraw and auxiliary materials, mild reaction conditions, high yield and environmental protection.

Method for synthesizing pyridoxal phosphate

The present invention discloses a method for synthesizing pyridoxal phosphate (5'-pyridoxal phosphate). According to the method, pyridoxine hydrochloride is used as a starting material, and is oxidized under mild reaction conditions to obtain a pyridoxal acidic salt, and a phosphate esterification reaction is carried out with a phosphate esterification reagent to obtain pyridoxal phosphate. According to the present invention, the method has advantages of easily-available raw materials, simple route, low toxicity, less side-reaction, easy product separation, easy product characterizing, high yield and the like.

Thermodynamical characteristics of the reaction of pyridoxal-5'-phosphate with L-amino acids in aqueous buffer solution

The reaction of pyridoxal-5'-phosphate with L-isomers of alanine, lysine, arginine, aspartic acid, glutamic acid, and glycine in phosphate buffer solution was studied by absorption spectroscopy and the calorimetry of dissolution at physiological acidity of the medium (pH 7.35). The formation constants of Schiff bases during reactions and changes in Gibbs energy, enthalpy, and entropy were determined. It was shown that the formation constant of the Schiff base and its spectral properties depend on the nature of the bound amino acid. The progress of the reaction with a majority of amino acids is governed by the entropy factor due to the predominant role of the dehydration effect of the reaction center of amino acids during chemical reactions. The intramolecular electrostatic interaction of an ionized phosphate group with the positively charged amino group on the end of the chain of amino acid residue stabilizes the Schiff bases formed by lysine and arginine. The extinction coefficient of the base, equilibrium constant, and the exothermic effect of the reaction then increase. The excess negative charge on the end of the chain of amino acid residues of aspartic and glutamic acids destabilizes the molecule of the Schiff base. In this case, the equilibrium constant decreases and the endothermic effect of the reaction increases. Pleiades Publishing, Ltd., 2011.

Understanding non-enzymatic aminophospholipid glycation and its inhibition. Polar head features affect the kinetics of Schiff base formation

Non-enzymatic aminophospholipid glycation is an especially important process because it alters the stability of lipid bilayers and interferes with cell function and integrity as a result. However, the kinetic mechanism behind this process has scarcely been studied. As in protein glycation, the process has been suggested to involve the formation of a Schiff base as the initial, rate-determining step. In this work, we conducted a comparative kinetic study of Schiff base formation under physiological conditions in three low-molecular weight analogues of polar heads in the naturally occurring aminophospholipids O-phosphorylethanolamine (PEA), O-phospho-dl-serine (PSer) and 2-aminoethylphenethylphosphate (APP) with various glycating carbonyl compounds (glucose, arabinose and acetol) and the lipid glycation inhibitor pyridoxal 5′-phosphate (PLP). Based on the results, the presence of a phosphate group and a carboxyl group in α position respect to the amino group decrease the formation constant for the Schiff base relative to amino acids. On the other hand, esterifying the phosphate group with a non-polar substituent in APP increases the stability of its Schiff base. The observed kinetic formation constants of aminophosphates with carbonyl groups were smaller than those for PLP. Our results constitute an important contribution to understanding the competitive inhibition effect of PLP on aminophospholipid glycation.

Kinetic and thermodynamic study of the reaction of pyridoxal 5′-phosphate with L-tryptophan

The apparent rate constants for formation (k1) and hydrolysis (k2) of the Schiff bases formed by reaction of pyridoxal 5′-phosphate with L-tryptophan were determined at various pH values, at different temperatures and at constant ionic strength (0.1 M). Also obtained were the elementary rate constants for formation and hydrolysis of the Schiff bases corresponding to the different chemical species present in the media, and the pK values of the Schiff's bases. The activation and thermodynamic parameters for the formation and hydrolysis of the Schiff's bases also were determined. Some of the ΔH0 and ΔS0 values for the individual processes were found to be positive. In basic media the enthalpic factor is unfavorable but the entropie contribution leads to a negative ΔG0. Copyright

Schiff's Bases Formed between Pyridoxal 5'-Phosphate and 4-Aminobutanoic Acid. Kinetic and Thermodynamic Study

The overall and individual kinetic constants of formation (k1 and k1i) and hydrolysis (k2, kOH and k2i) of the Schiff's bases formed between pyridoxal 5'-phosphate (PLP) and 4-aminobutanoic acid (GABA) at 10, 20, 25, 30, and 37 deg C, a variable pH and a constant ionic strength of 0.1 M (1 M = 1 mol dm-3) were determined. The formation of a Schiff's base is an intramolecular acid-catalyzed process. The activation and thermodynamic parameters for the formation and hydrolysis of the Schiff's bases were also determined. ΔH and ΔS for the individual processes were all found to be negative.

Influence of the polarity of the medium on the catalysis of formation, rate of hydrolysis and stability of the Schiff bases formed by pyridoxal 5′-phosphate with L-tryptophan

The apparent rate constants of formation (k1) and hydrolysis (k2), and the equilibrium constant (KpH), of the Schiff bases formed by pyridoxal 5′-phosphate with L-tryptophan in water and different aqueous ethanol mixtures at a variable pH, 25 °C and an ionic strength of 0.1 M (1 M = 1 mol dm-3) were determined. The individual rate constants of formation and hydrolysis of the Schiff bases of the systems corresponding to the different chemical species present in the medium, as a function of its acidity, were also determined, as were the pK values for the Schiff bases. The influence of the solvent medium on the formation and hydrolysis rate constants of the Schiff bases is discussed.

Determination of the rates of formation and hydrolysis of the schiff bases formed by pyridoxal 5′-phosphate with L-tryptophan and its methyl and n-butyl esters

The apparent rate constants of the formation (k1) and hydrolysis (k2) of the Schiff bases formed by pyridoxal 5′-phosphate with L-tryptophan and their methyl and n-butyl esters at a variable pH, 25 °C, and an ionic strength of 0.1 M were determined, along with the equilibrium constant (KpH). The individual rate constants of formation and hydrolysis of the Schiff bases of systems corresponding to different chemical species present in the medium as a function of its acidity were also determined, as were the pK values for the Schiff bases. The influence of the α-carboxyl group on the formation and hydrolysis constants of the Schiff bases, and also on their pK values, is demonstrated.