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Streptocinnamides A and B, Depsipeptides from Streptomyces sp. KMM 9044

A new structural group of antibiotics produced by a new strain Streptomyces sp. KMM 9044 was discovered as a result of teamwork of scientists from the Institute of Bioorganic Chemistry (IBCh RAS) and the Elyakov Pacific Institute of Bioorganic Chemistry (TIBOCh RAS).

Makarieva TN, Romanenko LA, Mineev KS, Shubina LK, Guglya EB, Kalinovskaya NI, Ivanchina NV, Guzii AG, Belozerova OA, Kovalchuk SI, Popov RS, Denisenko VA, Mikhailov VV, Babenko VV, Ilina EN, Malakhova MV, Terekhov SS, Kudzhaev AM, Dmitrenok PS, Yampolsky IV & Stonik VA

The strain from the Collection of Marine Microorganisms of the TIBOCh RAS ​​was isolated from marine sediments collected near the northwestern part of the Sea of ​​Japan in 2009. During the subsequent cultivation of the strain in the marine environment, two compounds with antibacterial activity were isolated. The structure of these compounds was established using the NMR and HRMS methods and also confirmed by a series of chemical transformations. The family of new compounds are chlorinated cyclic depsiheptapeptides containing 3-hydroxy-4-chlorvaline and 4-acetoxy-5-methylproline, non- standard amino acids in the depsipeptide macrocyclic structure and a glyceric acid residue. An interesting property of these antibiotics is the strong selective inhibition of a number of Gram-positive bacteria: Micrococcus sp. (MIC 6 ng/ml, strain KMM 1467), Arthrobacter sp. (MIC 20 ng/ml, strain ATCC 21022) and Mycobacterium smegmatis (MIC 300 ng/ml, strain MC2 155).
The results are published in Organic Letters .

 

july 1