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J Am Chem Soc. 2008 Nov 19;130(46):15260-1. doi: 10.1021/ja807192u. Epub 2008 Oct 28.

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

Author information

1
Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, Boston, Massachusetts 02115, USA.

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).

PMID:
18954141
PMCID:
PMC2631159
DOI:
10.1021/ja807192u
[Indexed for MEDLINE]
Free PMC Article

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