Anton P. Tyurin

Institute of Bioorganic Chemistry

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Vladimir A. Korshun

Institute of Bioorganic Chemistry

Vera A. Alferova

Institute of Bioorganic Chemistry

Anna A. Baranova

Institute of Bioorganic Chemistry

Alexey A. Chistov

Institute of Bioorganic Chemistry

Maxim V. Shuvalov

Lomonosov Moscow State University

Mikhail V. Biryukov

Institute of Systematics and Ecology of Animals

F.M. Dolgushin

NS Kurnakova Institute of General and Inorganic Chemistry

Stanislav S. Terekhov

Institute of Bioorganic Chemistry

Igor A. Ivanov

Institute of Bioorganic Chemistry

Olda A. Lapchinskaya

Gause Institute of New Antibiotics Russian Academy of Medical Sciences

Cooperative Institutions

Russian Academy of Sciences

Institute of Bioorganic Chemistry

Lomonosov Moscow State University

Gause Institute of New Antibiotics Russian Academy of Medical Sciences

Institute of Bioorganic Chemistry

Moscow State University

Academy of Medical Sciences

A. N. Nesmeyanov Institute of Organoelement Compounds

N.D. Zelinsky Institute of Organic Chemistry

Skolkovo Institute of Science and Technology

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CCDC 1897829: Experimental Crystal Structure Determination

The Cambridge Structural Database (2019)

E. V. Balagurova F.M. Dolgushin Anton P. Tyurin Alexander F. Smol’yakov I.T. Chizhevsky

10.5517/ccdc.csd.cc21pv9x

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Chemical Elicitors of Antibiotic Biosynthesis in Actinomycetes

Microorganisms (2018)

Anton P. Tyurin Vera A. Alferova Vladimir A. Korshun

Whole genome sequencing of actinomycetes has uncovered a new immense realm of microbial chemistry and biology. Most biosynthetic gene clusters present in genomes were found to remain “silent” under standard cultivation conditions. Some small molecules—chemical elicitors—can be used to induce the biosynthesis of antibiotics in actinobacteria and to expand the chemical diversity of secondary metabolites. Here, we outline a brief account of the basic principles of the search for regulators of this type and their application.

Chemical Biology

Secondary metabolism

10.3390/microorganisms6020052

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Citations (29)

1,2-Bis(diphenylphosphino)ethane-containing commo-ferracarboranes of unusual structure

Russian Chemical Bulletin (2019)

E. V. Balagurova F.M. Dolgushin Anton P. Tyurin Alexander F. Smol’yakov I.T. Chizhevsky

10.1007/s11172-019-2589-x

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Citations (3)

Gausemycins A,B – Cyclic Lipoglycopeptides from Streptomyces Sp.

Anton P. Tyurin Vera A. Alferova Alexander S. Paramonov Maxim V. Shuvalov Gulnara K. Kudryakova

We report a novel family of natural lipoglycopeptides produced by Streptomyces sp. INA-Ac-5812. Two major components of the mixture, named gausemycins A and B, were isolated, and their structures were elucidated. The com-pounds are cyclic peptides with a unique peptide core and several remarkable structural features, including unusual posi-tions of D-amino acids, lack of the Ca2+-binding Asp-X-Asp-Gly (DXDG) motif, tyrosine glycosylation with arabinose, presence of 2-amino-4-hydroxy-4-phenylbutyric acid (Ahpb) and chlorinated kynurenine (ClKyn), N-acylation of the or-nithine side chain. These major components of the peptide antibiotic family have pronounced activity against Gram-positive bacteria. The mechanism of action of gausemycins was explored by a number of methods, showing significant differences compared to glycopeptides and related lipopeptides. Gausemycins exhibit only slight Ca2+-dependence of an-timicrobial activity and induce no pore formation at low concentrations. Moreover, there is no detectable accumulation of cell wall biosynthesis precursors under treatment with gausemycins.

Cyclic peptide

10.26434/chemrxiv.13012814

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Synthesis of 11-vertex cobalt bis(diphenylphosphine) complexes based on medium-size non-icosahedral carborane 5,6-nido-C2B8H12. Molecular structure of complex [1,1-{κ2-1′,2′-Ph2P(CH2)2PPh2}-1-H-isonido-1,2,4-CoC2B8H10]

Russian Chemical Bulletin (2024)

E. V. Balagurova Anton P. Tyurin Ivan A. Godovikov F.M. Dolgushin I.T. Chizhevsky

Carborane

Diphenylphosphine

10.1007/s11172-024-4406-4

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CCDC 922916: Experimental Crystal Structure Determination

The Cambridge Structural Database (2013)

Anton P. Tyurin F.M. Dolgushin Alexander F. Smol’yakov Ivan D. Grishin Dmitrii I. D’yachihin

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/cczzchs

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Imaging-based profiling for elucidation of antibacterial mechanisms of action

Anna A. Baranova Vera A. Alferova Vladimir A. Korshun Anton P. Tyurin

In this review, we aim to summarize experimental data and approaches to identifying cellular targets or mechanisms of action of antibacterials based on imaging techniques. Imaging-based profiling methods such as bacterial cytological profiling, dynamic bacterial morphology imaging and others have become a useful research tool for mechanistic studies of new antibiotics as well as combinations with conventional ones and other therapeutic options. The main methodological, experimental details and obtained results are summarized and discussed. The review covers the literature up to Feb 2024.

Profiling (computer programming)

10.26434/chemrxiv-2024-w4vth

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Inside Cover: Gausemycins A,B: Cyclic Lipoglycopeptides from Streptomyces sp. (Angew. Chem. Int. Ed. 34/2021)

Angewandte Chemie International Edition (2021)

Anton P. Tyurin Vera A. Alferova Alexander S. Paramonov Maxim V. Shuvalov Gulnara K. Kudryakova

A new lipoglycopeptide antibiotic family with unique structural features and pronounced activity against Gram-positive bacteria is described by Stanislav S. Terekhov, Zakhar O. Shenkarev, Vladimir A. Korshun, and co-workers in their Research Article on page 18694. Gausemycins are intrinsically fluorescent compounds with an original mode of antibacterial action. Analysis of the biosynthetic gene cluster revealed unusual enzymology, involved in the formation of a previously unknown nonproteinogenic amino acid.

INT

Gene cluster

Mode of Action

10.1002/anie.202107693

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Synthesis of 5-oxo-1-(5-R-1,3,4-thiadiazol-2-yl)pyrrolidine-3-carboxylic acids

Russian Chemical Bulletin (2023)

С. А. Серков Natalya V. Sigay N. N. Kostikova Anton P. Tyurin N. G. Kolotyrkina

Pyrrolidine

Itaconic acid

10.1007/s11172-023-3966-z

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Doubly Protonated Species Collision Induced Dissociation for Identification of Isocyclosporins

Anna A. Baranova Alexey A. Chistov Maxim V. Shuvalov Anton P. Tyurin Mikhail V. Biryukov

Nonribosomal cyclopeptide cyclosporin A (CsA), produced by fungus Tolypocladium inflatum , is an extremely important immunosuppressive drug used in organ transplantations and for therapy of autoimmune diseases. Here we report for the first time production of CsA, along with related cyclosporins B and C, by Tolypocladium inflatum strains of marine origin (White Sea). Cyclosporins A–C contain an unusual amino acid, (4 R )-4-(( E )-2-butenyl)-4, N -dimethyl-l-threonine (MeBmt), and are prone to isomerization to non-active isocyclosporine by N→O acyl shift of valine connected to MeBmt in acidic conditions. CsA and isoCsA are not distinguishable in MS analysis of [M+H] + ions due to the rapid [CsA+H] + →[isoCsA+H] + conversion. We found that the N→O acyl shift is completely suppressed in cyclosporine [M+2H] 2+ ions, and their MS/MS fragmentation can be used for rapid and unambiguous analysis of cyclosporins and isocylosporins. The fragmentation patterns of [CyA+2H] 2+ and [isoCyA+2H] 2+ ions were analyzed and explained. The developed approach could be useful for MS analysis of other peptides containing β-hydroxy-α-amino acids.

Cyclosporins

Frog Skin

Fragmentation

10.26434/chemrxiv.12919235.v1

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