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Investigating the initial steps in the biosynthesis of cyanobacterial sunscreen scytonemin.


ABSTRACT: 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).

SUBMITTER: Balskus EP 

PROVIDER: S-EPMC2631159 | biostudies-literature | 2008 Nov

REPOSITORIES: biostudies-literature

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Investigating the initial steps in the biosynthesis of cyanobacterial sunscreen scytonemin.

Balskus Emily P EP   Walsh Christopher T CT  

Journal of the American Chemical Society 20081028 46


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 framewor  ...[more]

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