Abstract
In the course of screening new streptomycete strains, the strain Streptomyces sp. Cl 58-27 caught our attention due to its interesting secondary metabolite production profile. Here, we report the isolation and characterization of an ansamycin natural product that belongs structurally to the already known kendomycins. The structure of the new kendomycin E was elucidated using NMR spectroscopy, and the corresponding biosynthetic gene cluster was identified by sequencing the genome of Streptomyces sp. Cl 58-27 and conducting a detailed analysis of secondary metabolism gene clusters using bioinformatic tools.
Highlights
Polyketide natural products are a highly diverse group of compounds with a wide range of applications, for example as antibiotics, immunosuppressants or anticancer chemotherapeutics [1,2,3,4]
Modular type I polyketide synthases (PKSs), for example, consist of linearly arranged obligatory ketosynthase (KS), acetyl carrier protein (ACP) and acyl transferase (AT) domains, as well as optional ketoreductase (KR), dehydratase (DH), enoyl reductase (ER), methyltransferase (MT) and thioesterase (TE) domains grouped into modules, each performing one elongation and ketoreduction step
Concerning the absolute stereochemistry of the new kendomycin derivative, it was assumed that all stereocenters coincide with the stereochemistry previously found in kendomycin [(−)-TAN 2162] (2) and kendomycins B–D, which was elucidated by X-ray crystallography and advanced Mosher’s method [8], [13]
Summary
Polyketide natural products are a highly diverse group of compounds with a wide range of applications, for example as antibiotics, immunosuppressants or anticancer chemotherapeutics [1,2,3,4]. These highly oxygenated compounds are produced by multimodular enzymes called polyketide synthases (PKSs) that click together starter units such as acetyl-CoA with malonyl-CoA extender units and carry out modifications through domains such as ketoreductases, dehydratases or enoyl reductases, leading to a vast supply of structurally diverse molecules [5]. Three more derivatives (kendomycins B–D) have been discovered which differ in methylation degree and the presence of a thiomethyl group or N-acetyl-L-cysteine (NAC)
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