Pyrrole-2-carboxylic acid

Pyrrole-2-carboxylic acid  File:Pyrrole 2-carboxylic acid.svg

Names
Other names

2-Mialine, 2-Minaline, Minalin, Minaline

Identifiers

CAS Number

* 634-97-9 Y

3D model (JSmol)

* Interactive image

Beilstein Reference

| 80825
ChEBI |

* CHEBI:36751

ChEMBL |

* ChEMBL509027

ChemSpider |

* 11963

DrugBank |

* DB02543

EC Number |

* 211-221-9

Gmelin Reference

| 101562
KEGG |

* C05942

PubChem CID

* 12473

InChI

* InChI=1S/C5H5NO2/c7-5(8)4-2-1-3-6-4/h1-3,6H,(H,7,8)

Key: WRHZVMBBRYBTKZ-UHFFFAOYSA-N

SMILES

* C1=CNC(=C1)C(=O)O

Properties

Chemical formula

| C5H5NO2
Molar mass | 111.100 g·mol−1
Appearance  | white solid
Melting point |  206 °C (403 °F; 479 K)
Hazards
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H315, H319, H335

GHS precautionary statements

| P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Pyrrole-2-carboxylic acid is an organic compound with the formula HNC4H3CO2H. It is one of two monocarboxylic acids of pyrrole. It is a white solid. It arises in nature by dehydrogenation of the amino acid proline.[1] It also arises by carboxylation of pyrrole.[2] The ethyl ester of this acid is readily prepared from pyrrole.[3]

## Metabolism

In bacteria including Arthrobacter and Rhodococcus species, a specific enzyme, pyrrole-2-carboxylate monooxygenase converts pyrrole-2-carboxylic acid to its 5-hydroxypyrrole derivative.[4][5]

1. REDIRECT Template:Chemical reaction

The enzyme uses nicotinamide adenine dinucleotide as a cofactor.

## References

1. ↑ Thomas, Michael G.; Burkart, Michael D.; Walsh, Christopher T. (2002). "Conversion of L-Proline to Pyrrolyl-2-Carboxyl-S-PCP during Undecylprodigiosin and Pyoluteorin Biosynthesis". Chemistry & Biology 9 (2): 171–184. doi:10.1016/S1074-5521(02)00100-X. PMID 11880032.
2. ↑ Wieser, Marco; Yoshida, Toyokazu; Nagasawa, Toru (2001). "Carbon dioxide fixation by reversible pyrrole-2-carboxylate decarboxylase and its application". Journal of Molecular Catalysis B: Enzymatic 11 (4–6): 179–184. doi:10.1016/S1381-1177(00)00038-2.
3. ↑ Denis M. Bailey, Robert E. Johnson, Noel F. Albertson (1971). "Ethyl Pyrrole-2-Carboxylate". Organic Syntheses 51: 100. doi:10.15227/orgsyn.051.0100.
4. ↑ "Purification and characterization of a pyrrole-2-carboxylate oxygenase from Arthrobacter strain Py1". Biological Chemistry Hoppe-Seyler 375 (3): 211–8. March 1994. PMID 8011178.
5. ↑ "Two-component flavin-dependent pyrrole-2-carboxylate monooxygenase from Rhodococcus sp". European Journal of Biochemistry 249 (3): 739–47. November 1997. doi:10.1111/j.1432-1033.1997.t01-1-00739.x. PMID 9395321.

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Pyrrole-2-carboxylic_acid&oldid=4358025"
*[CID]: Compound ID
*[H315]: Causes skin irritation
*[H319]: Causes serious eye irritation
*[H335]: May cause respiratory irritation
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P337+313]: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …