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Indigoidine

Indigoidine is a science topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Indigoidine rather than just read about it. In short: 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.

Indigoidine — main illustration
Indigoidine — illustration

Key takeaways

  • Indigoidine belongs to science; place it in that map before memorising details.
  • Learn the definition first, then one example that makes the definition concrete.
  • Connect Indigoidine to a quantity you can measure, compute or draw — that is where exam questions come from.
  • Reproduce the core statement of Indigoidine from memory before moving on to harder problems.

Reference excerpt

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.

History An early report on indigo-blue pigment-producing bacteria was published by Heinr Claessen in 1890, describing a Bacillus isolated from water that produced an indigo-blue dye. 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. In 1979, Carl-Gerd Dieris and H.-D. Scharf described another synthesis of the compound.

Occurrence Indigoidine occurs in the following species of bacteria:

Arthrobacter atrocyaneus Arthrobacter crystallopoietes Arthrobacter polychromogones Corynebacterium insidiosum Erwinia chrysanthemi renamed to Dickea dadantii Vogesella indigofera previously Bacillus indigoferus and Pseudomonas indigofera

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.

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.

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.

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

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

See also Indigo dye – C16H10N2O2 Indigotin I – C16H8N2Na2O8S2

Literature Carl-Gerd Dieris: Zur Frage der Luminiszenz von thermooxidativ geschädigten Polycarpolaktam. Eine neue Synthese des Bakterienfarbstoffes Indigoidin und seiner Tetra-N-alkylderivate. 1980. Hans Günter Schlegel: Allgemeine Mikrobiologie. Thieme Verlagsgruppe, Stuttgart 1992, ISBN 978-3-13-444607-4. Reverchon, Sylvie; Rouanet, Carine; Expert, Dominique; Nasser, William (2002-01-02). "Characterization of Indigoidine Biosynthetic Genes in Erwinia chrysanthemi and Role of This Blue Pigment in Pathogenicity". Journal of Bacteriology. 184 (3): 654–665. doi:10.1128/JB.184.3.654-665.2002. PMC 139515. PMID 11790734. Christin Schönfeld: Charakterisierung und biochemische Analyse der Indigoidin Synthease BpsA aus S. lavendulae ATCC 11924. Masterarbeit, Philipps-Universität Marburg 2012. M. Müller, S. Ausländer, D. Ausländer, C. Kemmer, M. Fussenegger: A novel reporter system for bacterial and mammalian cells based on the non-ribosomal peptide indigoidine. Metabolic Engineering 14/2012, S. 325–335 (doi:10.1016/j.ymben.2012.04.002). H. Kobayashi, Y. Nogi, K. Hirokoshi: New violet 3,3'-bipyridyl pigment purified from deep-sea microorganism Shewanella violacea DSS12. In: Extremophiles Nr. 11(2)/2012, S. 245–250. PMID 17102923.

References

Illustrations

Indigoidine illustration
Indigoidine: Biosynthesis of indigoidin
Biosynthesis of indigoidin
Indigoidine: N5,N5′-Didodecylindigoidine
N5,N5′-Didodecylindigoidine

Worked examples

Example 1 — a first encounter with Indigoidine

Start with the simplest possible case. Write down what Indigoidine claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In science, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Indigoidine before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Indigoidine ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Indigoidine

In research
Indigoidine appears in science research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry
Engineering practice reuses Indigoidine in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom
Indigoidine is common in secondary-school and first-year university syllabi. It links to neighbouring topics Aromatic amines, Aromatic ketones, Natural dyes, so understanding it makes those chapters shorter.
In everyday life
Look for Indigoidine outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.
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How to study Indigoidine in 20 minutes

  1. Read the reference excerpt below once, without taking notes.
  2. Close the page and write down what Indigoidine means in your own words.
  3. Compare your version with the excerpt and mark what you missed.
  4. Work through the three examples above with pen and paper.
  5. Explain Indigoidine out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Indigoidine in simple terms?

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.

Why does Indigoidine matter?

Because it connects several science ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Indigoidine?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Indigoidine.

Tags

  • Aromatic amines
  • Aromatic ketones
  • Natural dyes
  • Pyridines

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