Angewandte Chemie - International Edition

, volume 60 , issue 34 , pages 18694-18703

Gausemycins A,B: Cyclic Lipoglycopeptides from Streptomyces sp.**

Anton P Tyurin ^{1, 2}

Vera A Alferova ^{1, 2, 3, 4}

Alexander S Paramonov ^{3, 4}

Maxim V Shuvalov ^{1, 2, 5, 6}

Gulnara K Kudryakova ^{1, 2}

E. A. Rogozhin ^{1, 2, 3, 4}

Alexander Zherebker ^{7, 8}

V. A. Brylev ^{3, 4}

Alexey A. Chistov ^{3, 4}

Anna A Baranova ^{1, 2, 3, 4}

Mikhail V Biryukov ^{1, 2, 9, 10}

Igor A Ivanov ^{3, 4}

Igor A Prokhorenko ^{1, 2, 3, 4}

Natalia Grammatikova ^{1, 2}

Tatyana V Kravchenko ^{1, 2, 3, 4}

Elena B. Isakova ^{1, 2}

Elena P. Mirchink ^{1, 2}

Elena G Gladkikh ^{1, 2}

E. V. Svirshchevskaya ^{3, 4}

A. V. Mardanov ^{11, 12}

A. V. Beletsky ^{11, 12}

Milita V Kocharovskaya ^{3, 4, 13, 14}

Valeriya V Kulyaeva ^{1, 2}

Alexander S. Shashkov ^{15, 16}

D. S. Tsvetkov ¹⁵

Dmitry E Tsvetkov ¹⁶

Nikolay E. Nifantiev ^{15, 16}

Alexander Apt ^{17, 18}

Konstantin B Majorov ^{17, 18}

Svetlana S. Efimova ^{19, 20}

N. V. Ravin ^{11, 12}

Evgeny Nikolaev ^{7, 8}

Olga S Ostroumova ^{19, 20}

Genrikh S Katrukha ^{1, 2}

Olda A Lapchinskaya ^{1, 2}

Olga A. Dontsova ^{3, 4, 5, 6, 7, 8}

Stanislav S Terekhov ^{3, 4, 5, 6}

Ilya A Osterman ^{5, 6, 7, 8}

Z. O. Shenkarev ^{3, 4, 13, 14}

Vladimir A. Korshun ^{1, 2, 3, 4}

Hide authors affiliations Show authors affiliations: 20 affiliations

Gause Institute of New Antibiotics B. Pirogovskaya 11 119021 Moscow Russia |

Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry RAS Miklukho-Maklaya 16/10 117997 Moscow Russia |

⁴

Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry RAS Miklukho-Maklaya 16/10 117997 Moscow Russia |

⁵

Department of Chemistry Lomonosov Moscow State University Leninskie Gory 1–3 119992 Moscow Russia |

⁶

Department of Chemistry Lomonosov Moscow State University Leninskie Gory 1–3 119992 Moscow Russia |

⁷

Skolkovo Institute of Science and Technology Nobel Street 3, Skolkovo 143026 Moscow Region Russia |

⁸

Skolkovo Institute of Science and Technology Nobel Street 3, Skolkovo 143026 Moscow Region Russia |

⁹

Department of Biology Lomonosov Moscow State University Leninskie Gory 1–3 119992 Moscow Russia |

¹⁰

Department of Biology Lomonosov Moscow State University Leninskie Gory 1–3 119992 Moscow Russia |

¹¹

Institute of Bioengineering Research Center of Biotechnology of the Russian Academy of Sciences Leninsky Prospect 33-2 119071 Moscow Russia |

¹²

Institute of Bioengineering Research Center of Biotechnology of the Russian Academy of Sciences Leninsky Prospect 33-2 119071 Moscow Russia |

¹³

Moscow Institute of Physics and Technology Institutsky Lane 9, Dolgoprydny 141700 Moscow region Russia |

¹⁴

Moscow Institute of Physics and Technology Institutsky Lane 9, Dolgoprydny 141700 Moscow region Russia |

¹⁵

Zelinsky Institute of Organic Chemistry RAS Leninsky Prospect 47 119991 Moscow Russia |

¹⁶

Zelinsky Institute of Organic Chemistry RAS Leninsky Prospect 47 119991 Moscow Russia |

¹⁷

Central Tuberculosis Research Institute Yauzskaya Alley 2 107564 Moscow Russia |

¹⁸

Central Tuberculosis Research Institute Yauzskaya Alley 2 107564 Moscow Russia |

¹⁹

Institute of Cytology RAS Tikhoretsky Prospect 4 194064 St. Petersburg Russia |

²⁰

Institute of Cytology RAS Tikhoretsky Prospect 4 194064 St. Petersburg Russia |

Publication type: Journal Article

Publication date: 2021-06-22

Wiley

Angewandte Chemie - International Edition

scimago Q1

wos Q1

SJR: 5.550

CiteScore: 27.6

Impact factor: 16.9

ISSN: 14337851, 15213773

DOI: 10.1002/anie.202104528

Copy DOI

PubMed ID: 34009717

General Chemistry

Catalysis

Abstract

We report a novel family of natural lipoglycopeptides produced byStreptomycessp. INA‐Ac‐5812. Two major components of the mixture, named gausemycins A and B, were isolated, and their structures were elucidated. The compounds are cyclic peptides with a unique peptide core and several remarkable structural features, including unusual positions ofd‐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), and N‐acylation of the ornithine side chain. Gausemycins have pronounced activity against Gram‐positive bacteria. Mechanistic studies highlight significant differences compared to known glyco‐ and lipopeptides. Gausemycins exhibit only slight Ca²⁺‐dependence of activity and induce no pore formation at low concentrations. Moreover, there is no detectable accumulation of cell wall biosynthesis precursors under treatment with gausemycins.

Found

3 citations

Poshvina D

PhD in Biological/biomedical sciences

18 publications, 100 citations

h-index: 6

University of Tyumen

2 citations

Vasilchenko Alexey

🤝

PhD in Biological/biomedical sciences

70 publications, 880 citations, 45 reviews

h-index: 16

University of Tyumen

Research interests

Atomic force microscopy

Quorum sensing

1 citation

Krylov Vadim

DSc in Chemistry

106 publications, 1 676 citations

h-index: 25

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

1 citation

Eliseev O

87 publications, 725 citations, 3 reviews

h-index: 17

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Peoples' Friendship University of Russia

1 citation

Baranova Anna

PhD in Education

11 publications, 38 citations

h-index: 2

Mari State University

1 citation

Kononov Leonid

DSc in Chemistry

150 publications, 2 081 citations, 28 reviews

h-index: 25

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Moscow Institute of Physics and Technology

1 citation

Chaliy Vasiliy

🥼

7 publications, 18 citations

h-index: 3

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Bauman Moscow State Technical University

Research interests

Density functional theory (DFT)

Molecular modeling

1 citation

Sakharov Alexey

37 publications, 527 citations

h-index: 9

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Tyurin A. P. et al. Gausemycins A,B: Cyclic Lipoglycopeptides from Streptomyces sp.** // Angewandte Chemie - International Edition. 2021. Vol. 60. No. 34. pp. 18694-18703.

GOST all authors (up to 50) Copy

Tyurin A. P. et al. Gausemycins A,B: Cyclic Lipoglycopeptides from Streptomyces sp.** // Angewandte Chemie - International Edition. 2021. Vol. 60. No. 34. pp. 18694-18703.

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BibTex (up to 50 authors) Copy

@article{2021_Tyurin,

author = {Anton P Tyurin and Vera A Alferova and Alexander S Paramonov and Maxim V Shuvalov and Gulnara K Kudryakova and E. A. Rogozhin and Alexander Zherebker and V. A. Brylev and Alexey A. Chistov and Anna A Baranova and Mikhail V Biryukov and Igor A Ivanov and Igor A Prokhorenko and Natalia Grammatikova and Tatyana V Kravchenko and Elena B. Isakova and Elena P. Mirchink and Elena G Gladkikh and E. V. Svirshchevskaya and A. V. Mardanov and A. V. Beletsky and Milita V Kocharovskaya and Valeriya V Kulyaeva and Alexander S. Shashkov and D. S. Tsvetkov and Dmitry E Tsvetkov and Nikolay E. Nifantiev and Alexander Apt and Konstantin B Majorov and Svetlana S. Efimova and N. V. Ravin and Evgeny Nikolaev and Olga S Ostroumova and Genrikh S Katrukha and Olda A Lapchinskaya and Olga A. Dontsova and Stanislav S Terekhov and Ilya A Osterman and Z. O. Shenkarev and Vladimir A. Korshun and others},

title = {Gausemycins A,B: Cyclic Lipoglycopeptides from Streptomyces sp.**},

journal = {Angewandte Chemie - International Edition},

year = {2021},

volume = {60},

publisher = {Wiley},

month = {jun},

url = {https://onlinelibrary.wiley.com/doi/10.1002/anie.202104528},

number = {34},

pages = {18694--18703},

doi = {10.1002/anie.202104528}

}

MLA

Cite this

MLA Copy

Tyurin, Anton P., et al. “Gausemycins A,B: Cyclic Lipoglycopeptides from Streptomyces sp.**.” Angewandte Chemie - International Edition, vol. 60, no. 34, Jun. 2021, pp. 18694-18703. https://onlinelibrary.wiley.com/doi/10.1002/anie.202104528.

Publisher

Wiley

Journal

Angewandte Chemie - International Edition

scimago Q1

wos Q1

SJR

5.550

CiteScore

27.6

Impact factor

16.9

ISSN

14337851 (Print)

15213773 (Electronic)

Labs

Laboratory of Nucleoprotein Chemistry, Department of Chemistry of Natural Compounds, Faculty of Chemistry

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