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Abstract
A photolabile carba(dethia) malonyl N‐acetylcysteamine derivative was devised and prepared for the trapping of biosynthetic polyketide intermediates following light activation. From the lasalocid A polyketide assembly in a mutant strain of the soil bacterium Streptomyces lasaliensis, a previously undetected cyclised intermediate was identified and characterised, providing a new outlook on the timing of substrate processing.
Highlights
polyketide synthases (PKSs) are classified as modular or iterative and into different types on the basis of their structural organization and modus operandi.[2]
[3] Over time key insights into PKS workings have been provided by molecular biology, enzymology, analytical chemistry and structural studies. [3b, 4] challenges in PKS studies remain; these are mainly associated with limitations in our ability to closely monitor the biocatalysis in its natural context and thereby determine the exact mechanism and order of enzymatic transformations
The probes are carba(dethia) N-acetylcysteamine (NAc) derivatives which mimic the acyl carrier protein (ACP)-malonyl extender units utilised in polyketide formation (2, Fig. 1) and have been utilised for in vitro and in vivo studies to shed light on previously unknown details of complex polyketide formation, such as that of polyethers, macrolides and
Summary
PKSs are classified as modular or iterative and into different types on the basis of their structural organization and modus operandi.[2]. In our group we have devised a chemical approach for polyketide biosynthetic investigations based on the use of ‘chain termination’ probes capable of intercepting PKS biosynthetic intermediates throughout product assembly.
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