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Liquid Carbon
Date: 2007-08-07 17:19
Subject: Bioluminescence.
Security: Public
Mood:Proteins
Tags:bio vs chem, books, hetchem, light, proteins


  I have read this wonderful book on bioluminescence Osamu Shimomura, the discoverer of the Green Fluorescent Protein and a man with 50 years of experience in the bioluminescence research. As biological as it is, the book is still a nice read for chemists as well.

  Luciferins are naturally occuring compounds that are oxidized in vivo with emission of light responsible for the bioluminescence. An example of such reaction in fireflies was recently posted by Greg at Carbontet. Here are the structures luciferins known to date:




  The biogenetic pathways of luciferins can be traced to amino acids (coelentrazine, Cypridina and firefly luciferins) or to terpenes (limpet, mushroom). There is also this peculiar stub of chlorophyll in dinoflagellate luciferin.

  The structure of fungal luciferin was deduced on the basis of known structure of panal (a preluciferin) and never published model activation studies made with 13C-labelled partial structure of panal. The luciferin is formed in reaction of acylated panal (compounds PS-A, PS-B and PS-C — O-decanoyl, O-dodecanoyl and O-tetradecanoyl derivatives, respectively) with a primary amine, usually ammonia or methylamine in vitro, unknown biogenic amine in vivo. Though absolute configuration of panal is not known, it can be deduced on the basis of some natural products of related origin, for which X-ray structures are published. This is what I did to put the stereocentres on the scheme. See, sometimes Liquidcarbon has unique material to offer.

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User: (Anonymous)
Date: 2007-08-07 18:50 (UTC)
Subject: (no subject)
cool! i especially like the bacterial luciferin, since i have a soft spot for thiazoles.
--psistarpsi
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Liquid Carbon
User: liquidcarbon
Date: 2007-08-07 20:53 (UTC)
Subject: (no subject)
Hey, it's achiral, but it isn't flat! I would expect you'd like coelenterazine the best.

There's a comment for you in the last Kutti's post.

What about thiazoles?
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Liquid Carbon
User: liquidcarbon
Date: 2007-08-07 20:53 (UTC)
Subject: (no subject)
I mean coelenterezaine is the most flat of them.
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User: (Anonymous)
Date: 2007-08-08 18:15 (UTC)
Subject: (no subject)
Can't say much about them. One of my projects deals with them, though...
--psi*psi
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User: (Anonymous)
Date: 2007-08-07 20:23 (UTC)
Subject: Kyle Finchsigmate Says:
I agree, that's pretty dope.
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Liquid Carbon
User: liquidcarbon
Date: 2007-08-07 20:35 (UTC)
Subject: Re: Kyle Finchsigmate Says:
Kyle, define "dope", please... I'm confused!
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User: (Anonymous)
Date: 2007-08-07 21:38 (UTC)
Subject: Re: Kyle Finchsigmate Says:
Well before the WWII, the primary meaning of the word dope used to be a "less-than-brilliant person" (durak).

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Liquid Carbon
User: liquidcarbon
Date: 2007-08-07 22:00 (UTC)
Subject: Re: Kyle Finchsigmate Says:
There was no NMR before WWII.
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