Indigoidine

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Indigoidine
Indigoidin.svg
Names
Systematic IUPAC name
(5E)-3-amino-5-(5-amino-2,6-dioxopyridin-3-ylidene)pyridine-2,6-dione
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
  • InChI=1S/C10H8N4O4/c11-5-1-3(7(15)13-9(5)17)4-2-6(12)10(18)14-8(4)16/h1-2,11H,12H2,(H,13,15,17)(H2,14,16,18)
    Key: YCZATMZTIWSFLZ-UHFFFAOYSA-N
  • C1=C(C(=O)NC(=O)C1=N)C2=C(NC(=O)C(=C2)N)O
Properties
C10H8N4O4
Molar mass 248,19 g·mol −1
Appearanceblue powder [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Indigoidine is an organic compound of the azaquinone group. It is a blue pigment produced by some bacterial species that excrete it into the surrounding medium.

Contents

History

Otto Voges researched and described the bacterial species Bacillus indigoferus in 1893, renamed after him to Vogesella indigofera , in Kiel, which continuously discolored the surrounding medium (water) from slightly bluish (24 hours) to royal blue (48 hours).

In 1964 and 1965, Nobel laureate Richard Kuhn and his colleagues published several articles in the scientific press on the occurrence, structure and synthesis of indigoidine. [2] [3] [4]

In 1979, Carl-Gerd Dieris and H.-D. Scharf described another synthesis of the compound. [5]

Occurrence

Indigoidine occurs in the following species of bacteria:

Synthesis

Indigoidine can be synthesized from citrazinic Acid (C6H5NO4), which is itself produced from citric acid and ammonia.

Biosynthesis

The biosynthesis of indigoidine starts from glutamine, which is enzymatically oxidized, cyclized to the heterocycle and dimerized. [6]

Biosynthesis of indigoidin Biosintesis de la indigoidina.png
Biosynthesis of indigoidin

The names for the segments A, Ox, A, T and Te refer to defined domains within the enzyme structure of the bpsA gene product BPSA. [7]

Properties

Physical properties

Indigoidine is a blue amorphous powder that is insoluble in water and most other solvents, but dissolves in hydrochloric acid, producing a royal blue color, and in hot sulfuric acid, producing an orange-brown color. [8]

Chemical properties

The color of indigoidine is attributed to an indigoid chromophore. NMR spectroscopic studies of derivatives confirmed the stated symmetrical structure. Because of the nitrogen atoms in the quinoid rings, indigoidine is classified as azaquinones.

Derivatives

N ,N -Didodecylindigoidine N5,N5'-Didodecylindigoidine.png
N ,N -Didodecylindigoidine

A derivative is the violet pigment N5,N5′-Didodecylindigoidine, (C34H56N4O4), which was isolated from the psychrophile bacteria Shewanella violacea DSS12. [9]

See also

Literature

References

  1. ↑ R. A. Abramovitch: The Chemistry of Heterocyclic Compounds. Pyridine and its Derivatives. John Wiley & Sons, New York 1974, ISBN 0-471-37915-8
  2. ↑ Kuhn, Richard; Bauer, Helmut; Knackmuss, Hans-Joachim; Kuhn, Daisy A.; Starr, Mortimer P. (1964-01-01). "Die Struktur der blauen Pigmente von Corynebacterium insidiosum, Arthrobacter atrocyaneus, Pseudomonas indigofera und Arthrobacter crystallopoietes". Die Naturwissenschaften. 51 (17): 409. Bibcode:1964NW.....51..409K. doi:10.1007/BF00609040.
  3. ↑ Kuhn, Richard; Bauer, Helmut; Knackmuss, Hans-Joachim (1965). "Struktur und Synthesen des Bakterienfarbstoffs Indigoidin". Chemische Berichte. 98 (7): 2139–2153. doi:10.1002/cber.19650980714. PMID   5849850.
  4. ↑ Kuhn, Richard; Starr, Mortimer P.; Kuhn, Daisy A.; Bauer, Helmut; Knackmuss, Hans-Joachim (1965-03-01). "Indigoidine and other bacterial pigments related to 3,3'-bipyridyl". Archiv für Mikrobiologie. 51 (1): 71–84. Bibcode:1965ArMic..51...71K. doi:10.1007/BF00406851. PMID   14347925.
  5. ↑ Dieris, C. -G.; Scharf, H. -D. (1979). "Eine neue Synthese des Bakterienfarbstoffs Indigoidin und seiner Tetra-N-alkyl-Derivate". Synthesis. 1979 (12): 948–950. doi:10.1055/s-1979-28883.
  6. ↑ Müller, Marius; Ausländer, Simon; Ausländer, David; Kemmer, Christian; Fussenegger, Martin (2012). "A novel reporter system for bacterial and mammalian cells based on the non-ribosomal peptide indigoidine". Metabolic Engineering. 14 (4): 325–335. doi:10.1016/j.ymben.2012.04.002. PMID   22543310.
  7. ↑ Takahashi, Hitoshi; Kumagai, Takanori; Kitani, Kyoko; Mori, Miwako; Matoba, Yasuyuki; Sugiyama, Masanori (2007). "Cloning and Characterization of a Streptomyces Single Module Type Non-ribosomal Peptide Synthetase Catalyzing a Blue Pigment Synthesis". Journal of Biological Chemistry. 282 (12). Elsevier BV: 9073–9081. doi: 10.1074/jbc.m611319200 . ISSN   0021-9258. PMID   17237222 . Retrieved May 1, 2025.
  8. ↑ Communications, EBCONT. "Indigoidin". RÖMPP, Thieme (in German). Retrieved May 1, 2025.
  9. ↑ New violet 3,3'-bipyridyl pigment purified from deep-sea microorganism Shewanella violacea DSS12. 2007. pp. 245–250.
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