487-90-1

Basic information

• Product Name: PORPHOBILINOGEN
• Synonyms: 5-(aminomethyl)-4-(carboxymethyl)-1h-pyrrole-3-propanoicaci;5-[AMINOMETHYL]-4-[CARBOXYMETHYL]-1H-PYRROLE-3-PROPANOIC ACID;PORPHOBILINOGEN;porphobilinogen (synth.);5-(aminomethyl)-4-(carboxymethyl)-1H-pyrrole-3-propionic acid;3-[5-(aminomethyl)-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid;3-[5-(aminomethyl)-4-(carboxymethyl)-1H-pyrrol-3-yl]propionic acid;5-(Aminomethyl)-4-(carboxymethyl)pyrrole-3-propionic acid
• CAS NO: 487-90-1
• Molecular Formula: C₁₀H₁₄N₂O₄
• Molecular Weight: 226.23
• EINECS: 207-666-3
• Product Categories: Porphyrins;Precursers;Amines;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;organic building block
• Mol File: 487-90-1.mol
• Article Data: 20

Chemical Properties

• Melting Point: 174-177℃
• Boiling Point: 479℃
• Flash Point: 243℃
• Appearance: light yellow to pink/powder
• Density: 1.421
• Vapor Pressure: 5.74E-10mmHg at 25°C
• Refractive Index: 1.621
• Storage Temp.: −20°C
• Solubility: Aqueous Base (Slightly), Acetonitrile (Slightly), DMSO (Slightly)
• PKA: 4.22±0.10(Predicted)
• Merck: 13,7681
• BRN: 220051
• CAS DataBase Reference: PORPHOBILINOGEN(CAS DataBase Reference)
• NIST Chemistry Reference: PORPHOBILINOGEN(487-90-1)
• EPA Substance Registry System: PORPHOBILINOGEN(487-90-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 8-10
• Hazardous Substances Data: 487-90-1(Hazardous Substances Data)

Usage

Description

PORPHOBILINOGEN, also known as hydroxymethylbilane, is an organic compound that serves as a crucial intermediate in the biosynthesis of heme, a vital component of hemoglobin and other hemoproteins. It is synthesized from glycine and succinyl-CoA in a series of enzymatic reactions. PORPHOBILINOGEN is found in the urine of patients with acute porphyria, a group of rare genetic disorders that affect the production of heme.

Uses

Used in Medical Diagnostics:
PORPHOBILINOGEN is used as a diagnostic marker for acute porphyria. The detection of PORPHOBILINOGEN in the urine of patients helps in the identification and monitoring of the disease, which can lead to appropriate treatment and management strategies.
Used in Research and Development:
PORPHOBILINOGEN is utilized as a research tool in the study of heme biosynthesis, hemoproteins, and related metabolic pathways. It aids in understanding the molecular mechanisms underlying various diseases and conditions associated with heme synthesis and function.
Used in Pharmaceutical Industry:
PORPHOBILINOGEN serves as a key intermediate in the production of heme and related compounds, which are essential for the development of drugs targeting heme metabolism and related disorders. It is also used in the synthesis of novel therapeutic agents for the treatment of acute porphyria and other related conditions.

Biochem/physiol Actions

Intermediate in the biosynthesis of heme.

Purification Methods

Porphobilinogen recrystallises as the monohydrate (pink crystals) from dilute NH4 OAc solutions of pH 4, and is dried in vacuo. The hydrochloride monohydrate has m 165-170o(dec) (from dilute HCl). [Jackson & MacDonald Can J Chem 35 715 1957, Westall Nature 170 614 1952, Bogarad J Am Chem Soc 75 3610 1953, Beilstein 22/14 V 210.]

InChI:InChI=1/C10H14N2O4/c11-4-8-7(3-10(15)16)6(5-12-8)1-2-9(13)14/h5,12H,1-4,11H2,(H,13,14)(H,15,16)

Upstream product

• 109820-76-0 3-(2-ethoxycarbonyl-ethyl)-4-ethoxycarbonylmethyl-5-aminomethyl-pyrrole-2-carboxylic acid ethyl ester; hydrochloride 
• 172667-50-4 methyl-4-nitro-5-acetoxy-7-<(tetrahydro-2H-pyran-2-yl)oxy>-heptanoate 
• 172667-51-5 2-cyano-3-<2-(tetrahydro-2H-pyran-2-yl)oxy> ethyl-4-(2-methoxycarbonylethyl)pyrrole 
• 172667-49-1 methyl 5-hydroxy-4-nitro-7-(tetrahydropyran-2'-yloxy)-heptanoate 
• 172667-52-6 2-cyano-3-(2-hydroxyethyl)-4-(2-methoxycarbonylethyl)pyrrole 
• 91567-90-7 2-cyano-3-(1-methoxycarbonylmethyl)-4-(2-methoxycarbonylethyl)pyrrole 
• 58822-20-1 3-(2-ethoxycarbonyl-ethyl)-4-ethoxycarbonylmethyl-5-(hydroxyimino-methyl)-pyrrole-2-carboxylic acid ethyl ester 
• 58822-21-2 5-cyano-3-(2-ethoxycarbonyl-ethyl)-4-ethoxycarbonylmethyl-pyrrole-2-carboxylic acid ethyl ester 
• 60857-11-6 5-aminomethyl-3-(2-ethoxycarbonyl-ethyl)-4-ethoxycarbonylmethyl-pyrrole-2-carboxylic acid ethyl ester 
• 24331-85-9 3-(2-ethoxycarbonyl-ethyl)-5-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid ethyl ester 
• 100061-37-8 3-(2-carboxy-ethyl)-4-carboxymethyl-5-(hydroxyimino-methyl)-pyrrole-2-carboxylic acid 
• 103565-31-7 5-aminomethyl-3-(2-carboxy-ethyl)-4-carboxymethyl-pyrrole-2-carboxylic acid 
• 3468-97-1 3-(2-carboxy-ethyl)-5-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid 
• 87721-24-2 ethyl 1-benzoyl-2-cyano-4-carbethoxyvinylpyrrole-3-acetate 

Downstream Products

• 71861-60-4 3,8,13,18-tetra-(2-carboxyethyl)-2,7,12,17-tetrakiscarboxymethyl-1-hydroxymethylbilane 
• 2624-63-7 coproporphyrinogen III 
• 553-12-8 protoporphyrin IX 
• 1867-62-5 uroporphyrinogen I 
• 1976-85-8 uroporphyrinogen III 

Relevant articles and documents

Structure of the heme biosynthetic Pseudomonas aeruginosa porphobilinogen synthase in complex with the antibiotic alaremycin

The recently discovered antibacterial compound alaremycin, produced by Streptomyces sp. A012304, structurally closely resembles 5-aminolevulinic acid, the substrate of porphobilinogen synthase. During the initial steps of heme biosynthesis, two molecules of 5-aminolevulinic acid are asymmetrically condensed to porphobilinogen. Alaremycin was found to efficiently inhibit the growth of both Gram-negative and Gram-positive bacteria. Using the newly created heme-permeable strain Escherichia coli CSA1, we are able to uncouple heme biosynthesis from bacterial growth and demonstrate that alaremycin targets the heme biosynthetic pathway. Further studies focused on the activity of alaremycin against the opportunistic pathogenic bacterium Pseudomonas aeruginosa. The MIC of alaremycin was determined to be 12 mM. Alaremycin was identified as a direct inhibitor of recombinant purified P. aeruginosa porphobilinogen synthase and had a Ki of 1.33 mM. To understand the molecular basis of alaremycin's antibiotic activity at the atomic level, the P. aeruginosa porphobilinogen synthase was cocrystallized with the alaremycin. At 1.75-A resolution, the crystal structure reveals that the antibiotic efficiently blocks the active site of porphobilinogen synthase. The antibiotic binds as a reduced derivative of 5-acetamido-4-oxo-5-hexenoic acid. The corresponding methyl group is, however, not coordinated by any amino acid residues of the active site, excluding its functional relevance for alaremycin inhibition. Alaremycin is covalently bound by the catalytically important active-site lysine residue 260 and is tightly coordinated by several active-site amino acids. Our data provide a solid structural basis to further improve the activity of alaremycin for rational drug design. Potential approaches are discussed. Copyright

Opportunities for Probing the Structure and Mechanism of Porphobilinogen Synthase by Raman Spectroscopy

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A CONVENIENT AND VERSATILE SYNTHESIS OF PORPHOBILINOGEN

Porphobilinogen (PBG, 1) was synthesized from 2-cyano-3,4-substituted pyrrole 3, which was obtained by condensation of α-acetoxynitro compound 4b with isocyanoacetonitrile (5), via functional group transformation, in good yield.

Deuterium isotope effects on porphobilinogen synthesis catalysed by 5-aminolaevulinic acid dehydratase

Deuteriation of 5-aminolaevulinic acid (ALA) at C-5 has no effect on the rate of porphobilinogen synthesis by ALA dehydratase from Bacillus subtilis but deuteriation at C-3 gave isotope effects on kcat and kcat/KM of 3.4 and 2.3 respectively. Reisolated ALA after 50% reaction shows no significant loss of deuterium at C-3, indicating that it is probably the first deprotonation at this carbon which is rate-determining. Copyright

Pseudomonas aeruginosa porphobilinogen synthase assembly state regulators: Hit discovery and initial SAR studies

Porphobilinogen synthase (PBGS) catalyzes the first common step in the biosynthesis of the essential heme, chlorophyll and vitamin B12 heme pigments. PBGS activity is regulated by assembly state, with certain oligomers exhibiting biological activity and others either partially or completely inactive, affording an innovative means of allosteric drug action. Pseudomonas aeruginosa PBGS is functionally active as an octamer, and inactive as a dimer. We have identified a series of compounds that stabilize the inactive P. aeruginosa dimer by a computational prescreen followed by native PAGE gel mobility shift analysis. From those results, we have prepared related thiadiazoles and evaluated their ability to regulate P. aeruginosa PBGS assembly state. ARKAT USA, Inc.