Angewandte Chemie - International Edition, volume 60, issue 34, pages 18694-18703

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

Tyurin Anton P ¹

Alferova Vera A ^{1, 2}

Paramonov Alexander S ²

Shuvalov Maxim V ^{1, 3}

Kudryakova Gulnara K ¹

Rogozhin E. A. ^{1, 2}

Zherebker Alexander ⁴

Brylev V. A. ²

Chistov Alexey A. ²

Baranova Anna A ^{1, 2}

Biryukov Mikhail V ^{1, 5}

Ivanov Igor A ²

Prokhorenko Igor A ^{1, 2}

Grammatikova Natalia ¹

Kravchenko Tatyana V ^{1, 2}

Isakova Elena B. ¹

Mirchink Elena P. ¹

Gladkikh Elena G ¹

Svirshchevskaya E. V. ²

Mardanov A. V. ⁶

Beletsky A. V. ⁶

Kocharovskaya Milita V ^{2, 7}

Kulyaeva Valeriya V ¹

Shashkov Alexander S. ⁸

Tsvetkov D. S. ⁸

Nifantiev Nikolay E. ⁸

Apt Alexander ⁹

Majorov Konstantin B ⁹

Efimova Svetlana S. ¹⁰

Ravin N. V. ⁶

Nikolaev Evgeny ⁴

Ostroumova Olga S ¹⁰

Katrukha Genrikh S ¹

Lapchinskaya Olda A ¹

Dontsova Olga A. ^{2, 3, 4}

Terekhov Stanislav S ^{2, 3}

Osterman Ilya A ^{3, 4}

Shenkarev Z. O. ^{2, 7}

Korshun Vladimir A. ^{1, 2}

Hide authors affiliations Show authors affiliations: 10 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 |

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

⁴

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

⁵

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

⁶

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

⁷

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

⁸

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

⁹

Central Tuberculosis Research Institute Yauzskaya Alley 2 107564 Moscow Russia |

¹⁰

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

Publication type: Journal Article

Publication date: 2021-06-22

Wiley

Journal: Angewandte Chemie - International Edition

Quartile SCImago

Quartile WOS

Impact factor: 16.6

ISSN: 14337851, 15213773

DOI: 10.1002/anie.202104528

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General Chemistry

Catalysis

Abstract

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 compounds are cyclic peptides with a unique peptide core and several remarkable structural features, including unusual positions of D-amino acids, lack of the Ca 2+ -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 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 Ca 2+ -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.

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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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RIS Copy

TY - JOUR

DO - 10.1002/anie.202104528

UR - https://doi.org/10.1002%2Fanie.202104528

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

T2 - Angewandte Chemie - International Edition

AU - Ivanov, Igor A

AU - Kravchenko, Tatyana V

AU - Isakova, Elena B.

AU - Mirchink, Elena P.

AU - Gladkikh, Elena G

AU - Kulyaeva, Valeriya V

AU - Shashkov, Alexander S.

AU - Katrukha, Genrikh S

AU - Lapchinskaya, Olda A

AU - Dontsova, Olga A.

AU - Tyurin, Anton P

AU - Alferova, Vera A

AU - Paramonov, Alexander S

AU - Shuvalov, Maxim V

AU - Kudryakova, Gulnara K

AU - Rogozhin, E. A.

AU - Zherebker, Alexander

AU - Brylev, V. A.

AU - Chistov, Alexey A.

AU - Baranova, Anna A

AU - Biryukov, Mikhail V

AU - Prokhorenko, Igor A

AU - Grammatikova, Natalia

AU - Svirshchevskaya, E. V.

AU - Mardanov, A. V.

AU - Beletsky, A. V.

AU - Kocharovskaya, Milita V

AU - Nifantiev, Nikolay E.

AU - Apt, Alexander

AU - Majorov, Konstantin B

AU - Efimova, Svetlana S.

AU - Ravin, N. V.

AU - Nikolaev, Evgeny

AU - Ostroumova, Olga S

AU - Terekhov, Stanislav S

AU - Osterman, Ilya A

AU - Shenkarev, Z. O.

AU - Korshun, Vladimir A.

AU - Tsvetkov, D. S.

PY - 2021

DA - 2021/06/22 00:00:00

PB - Wiley

SP - 18694-18703

IS - 34

VL - 60

SN - 1433-7851

SN - 1521-3773

ER -

BibTex |

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BibTex Copy

@article{2021_Tyurin,

author = {Igor A Ivanov and Tatyana V Kravchenko and Elena B. Isakova and Elena P. Mirchink and Elena G Gladkikh and Valeriya V Kulyaeva and Alexander S. Shashkov and Genrikh S Katrukha and Olda A Lapchinskaya and Olga A. Dontsova and 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 Prokhorenko and Natalia Grammatikova and E. V. Svirshchevskaya and A. V. Mardanov and A. V. Beletsky and Milita V Kocharovskaya 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 Stanislav S Terekhov and Ilya A Osterman and Z. O. Shenkarev and Vladimir A. Korshun and D. S. Tsvetkov},

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

journal = {Angewandte Chemie - International Edition},

year = {2021},

volume = {60},

publisher = {Wiley},

month = {jun},

url = {https://doi.org/10.1002%2Fanie.202104528},

number = {34},

pages = {18694--18703},

doi = {10.1002/anie.202104528}

}

MLA

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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://doi.org/10.1002%2Fanie.202104528.

Found error?

Publisher

Wiley

Journal

Angewandte Chemie - International Edition

Quartile SCImago

Quartile WOS

Impact factor

16.6

ISSN

14337851 (Print)
15213773 (Electronic)

Labs

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

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