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

被引：23

作者：

Tyurin, Anton P. ^{[1
]}

Alferova, Vera A. ^{[1
,2
]}

Paramonov, Alexander S. ^{[2
]}

Shuvalov, Maxim V. ^{[1
,3
]}

Kudryakova, Gulnara K. ^{[1
]}

Rogozhin, Eugene A. ^{[1
,2
]}

Zherebker, Alexander Y. ^{[4
]}

Brylev, Vladimir A. ^{[2
]}

Chistov, Alexey A. ^{[2
]}

Baranova, Anna A. ^{[1
,2
]}

Biryukov, Mikhail V. ^{[5
]}

Ivanov, Igor A. ^{[2
]}

Prokhorenko, Igor A. ^{[2
]}

Grammatikova, Natalia E. ^{[1
]}

Kravchenko, Tatyana V. ^{[1
,2
]}

Isakova, Elena B. ^{[1
]}

Mirchink, Elena P. ^{[1
]}

Gladkikh, Elena G. ^{[1
]}

Svirshchevskaya, Elena V. ^{[2
]}

Mardanov, Andrey V. ^{[6
]}

Beletsky, Aleksey V. ^{[6
]}

Kocharovskaya, Milita V. ^{[2
,10
]}

Kulyaeva, Valeriya V. ^{[1
]}

Shashkov, Alexander S. ^{[7
]}

Tsvetkov, Dmitry E. ^{[7
]}

Nifantiev, Nikolay E. ^{[7
]}

Apt, Alexander S. ^{[8
]}

Majorov, Konstantin B. ^{[8
]}

Efimova, Svetlana S. ^{[9
]}

Ravin, Nikolai V. ^{[6
]}

Nikolaev, Evgeny N. ^{[4
]}

Ostroumova, Olga S. ^{[9
]}

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, Zakhar O. ^{[2
,10
]}

Korshun, Vladimir A. ^{[1
,2
]}

机构：

[1] Gause Inst New Antibiot, B Pirogovskaya 11, Moscow 119021, Russia

[2] RAS, Shemyakin Ovchinnikov Inst Bioorgan Chem, Miklukho Maklaya 16-10, Moscow 117997, Russia

[3] Lomonosov Moscow State Univ, Dept Chem, Leninskie Gory 1-3, Moscow 119992, Russia

[4] Skolkovo Inst Sci & Technol, Nobel St 3, Skolkovo 143026, Moscow Region, Russia

[5] Lomonosov Moscow State Univ, Dept Biol, Leninskie Gory 1-3, Moscow 119992, Russia

[6] Russian Acad Sci, Res Ctr Biotechnol, Inst Bioengn, Leninsky Prospect 33-2, Moscow 119071, Russia

[7] RAS, Zelinsky Inst Organ Chem, Leninsky Prospect 47, Moscow 119991, Russia

[8] Cent TB Res Inst, Yauzskaya Alley 2, Moscow 107564, Russia

[9] RAS, Inst Cytol, Tikhoretsky Prospect 4, St Petersburg 194064, Russia

[10] Moscow Inst Phys & Technol, Inst Sky Lane 9, Dolgoprydny 141700, Moscow Region, Russia

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 34期

基金：

俄罗斯科学基金会;

关键词：

antibacterial activity; antibiotics; biosynthesis; lipoglycopeptides; structure elucidation; BIOSYNTHETIC GENE-CLUSTER; LIPOPEPTIDE ANTIBIOTICS; UNUSUAL GLYCOSYLATION; CELL-WALL; LIPID-II; COMPLEX; IDENTIFICATION; DAPTOMYCIN; MECHANISM; RAMOPLANIN;

D O I：

10.1002/anie.202104528

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 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.

引用

页码：18694 / 18703

页数：10

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