Uroporphyrinogen III

Base Information

• Chemical Name: Uroporphyrinogen III
• CAS No.: 1976-85-8
• Molecular Formula: C40H44 N4 O16
• Molecular Weight: 836.807
• DSSTox Substance ID: DTXSID40173444
• Nikkaji Number: J39.044E
• Wikipedia: Uroporphyrinogen_III
• Wikidata: Q897727
• Metabolomics Workbench ID: 37593
• Mol file: 1976-85-8.mol

Synonyms:Uroporphyrinogen III;Uroporphyrinogens

Chemical Property of Uroporphyrinogen III

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1163.6°Cat760mmHg
• PKA: 4.54±0.10(Predicted)
• Flash Point: 657.5°C
• PSA: 361.56000
• Density: 1.575g/cm³
• LogP: 2.25280
• XLogP3: 0
• Hydrogen Bond Donor Count: 12
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 20
• Exact Mass: 836.27523133
• Heavy Atom Count: 60
• Complexity: 1630

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=C(C(=C(N2)CC3=C(C(=C(N3)CC4=C(C(=C(N4)CC5=C(C(=C1N5)CCC(=O)O)CC(=O)O)CC(=O)O)CCC(=O)O)CC(=O)O)CCC(=O)O)CC(=O)O)CCC(=O)O
• General Description: Uroporphyrinogen III is a key intermediate in the biosynthesis of tetrapyrrole macrocycles, such as porphyrins, which play vital roles in bioenergetic processes and are hypothesized to be significant in the origin of life. It can form abiotically from acyclic reactants like d-aminolevulinic acid (ALA) and 5-methoxy-3-(methoxyacetyl)levulinic acid (1-AcOH) under moderate prebiotic conditions, bypassing the need for porphobilinogen (PBG). This suggests a plausible non-enzymatic pathway for its formation in early Earth environments.

Technology Process of Uroporphyrinogen III

There total 45 articles about Uroporphyrinogen III which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 8.0%

3,8,13,18-tetra-(2-carboxyethyl)-2,7,12,17-tetrakiscarboxymethyl-1-hydroxymethylbilane (71861-60-4) → uroporphyrinogen III (1976-85-8) + uroporphyrinogen I (1867-62-5)

Guidance literature:

With cosynthetase;

Reference yield:

aminomethylbilane → uroporphyrinogen III (1976-85-8) + uroporphyrinogen I (1867-62-5)

Guidance literature:

With phosphate buffer; deaminase-cosynthetase from Euglena gracilis; In water; at 37 ℃; for 17h; Product distribution; Mechanism; singly- and doubly-labelled bilanes; other products ratio for chemical cyclisation of aminomethylbilanes; identification of products as coproporphyrin octamethyl esters;

DOI:10.1039/P19810002786

Reference yield:

C20H25N3O8*H(1+) → uroporphyrinogen II (53790-13-9) + uroporphyrinogen III (1976-85-8) + uroporphyrinogen I (1867-62-5) + Uroporphyrinogen-IV (53790-14-0)

Guidance literature:

With phosphate buffer; deaminase-cosynthetase from Euglena gracilis; In water; at 16 ℃; for 16h; Mechanism; Product distribution; other products ratio with enzyme solution which had been heated (96 deg C, 5 min); labelling experiments; mechanism of biosynthesis of uroporphyrinogens;

DOI:10.1039/P19810002779

upstream raw materials:

3,3',3'',3'''-(19-aminomethyl-3,7,12,17-tetrakis-carboxymethyl-5,10,15,22,23,24-hexahydro-21H-biline-2,8,13,18-tetrayl)-tetrakis-propionic acid

3,8,13,18-tetra-(2-carboxyethyl)-2,7,12,17-tetrakiscarboxymethyl-1-hydroxymethylbilane

porphobilinogen

C₄₀H₄₆N₄O₁₇

Downstream raw materials:

protoporphyrin IX

coproporphyrinogen III

Refernces

Abiotic formation of uroporphyrinogen and coproporphyrinogen from acyclic reactants

10.1039/c0nj00716a

The research focuses on the abiotic formation of uroporphyrinogen and coproporphyrinogen from acyclic reactants, which are key precursors in the biosynthesis of tetrapyrrole macrocycles like porphyrins. These macrocycles are essential in various bioenergetic processes and are considered crucial for the origin of life. The study aimed to identify plausible prebiotic routes for forming these macrocycles, particularly addressing the challenge of forming the pyrrole precursor, porphobilinogen (PBG). The researchers successfully demonstrated a structure-directed route where d-aminolevulinic acid (ALA) reacts with 5-methoxy-3-(methoxyacetyl)levulinic acid (1-AcOH) under anaerobic conditions in water at moderate temperatures and pH levels, yielding uroporphyrinogen. This process bypasses the need for PBG, a significant hurdle in prebiotic chemistry, and suggests a possible prebiotic pathway for the formation of tetrapyrrole macrocycles. The study also showed that a different precursor could lead to the formation of coproporphyrinogen without the intermediacy of uroporphyrinogen. The chemicals used in this process include ALA, 1-AcOH, and their decarboxy analogues, which under specific conditions, resulted in the formation of uroporphyrinogen and coproporphyrinogen, respectively.

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