Investigating the Initial Steps in the Biosynthesis of Cyanobacterial Sunscreen Scytonemin

The cyanobacterial natural product scytonemin (1) functions as a sunscreen, absorbing harmful UV-A radiation. Using information from a recently identified gene cluster, we propose a biosynthetic route to this pigment. We also report the characterization of two enzymes, NpR1275 and NpR1276, which are...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2008-11, Vol.130 (46), p.15260-15261
Main Authors: Balskus, Emily P, Walsh, Christopher T
Format: Article
Language:English
Subjects:
Catalysis
Chromatography, High Pressure Liquid
Cyanobacteria - chemistry
Cyanobacteria - metabolism
Indoles - chemistry
Indoles - metabolism
Molecular Structure
Phenols - chemistry
Phenols - metabolism
Sunscreening Agents - chemistry
Sunscreening Agents - metabolism
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Summary:The cyanobacterial natural product scytonemin (1) functions as a sunscreen, absorbing harmful UV-A radiation. Using information from a recently identified gene cluster, we propose a biosynthetic route to this pigment. We also report the characterization of two enzymes, NpR1275 and NpR1276, which are involved in the initial stages of this pathway. A regioselective acyloin reaction between indole-3-pyruvic acid (4) and p-hydroxyphenylpyruvic acid (5) is a key step in assembling the carbon framework of a proposed monomeric scytonemin precursor (2).
ISSN:0002-7863
1520-5126
DOI:10.1021/ja807192u