Tetrahedron Letters, volume 60, issue 21, pages 1448-1451

Structure-activity studies of irumamycin type macrolides from Streptomyces sp. INA-Ac-5812

Publication typeJournal Article
Publication date2019-05-01
Quartile SCImago
Q3
Quartile WOS
Q3
Impact factor1.8
ISSN00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Three natural glycosylated macrolide compounds, known irumamycin 1 and X-14952B 2, as well as new isoirumamycin 3, were isolated from ethyl acetate mycelium extract of Streptomyces sp. INA-Ac-5812. Structures of the compounds were elucidated using 1D and 2D NMR. Isoirumamycin 3 was found to be an isomer of irumamycin with an 18-membered macrolactone ring instead of 20-membered macrolide in irumamycin. A previously unknown stereo configuration of irumamycin epoxide (C23, C24) and hemiketal (C3, C7) fragments was deduced from NMR data (ROESY/NOESY and HSQMBC). Cytotoxic, antifungal and antibacterial activities were studied for all isolated compounds. Comparison of the collected data showed crucial importance of 20-membered macrolactone ring for antimicrobial properties of this antibiotic family.

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Alferova V. A. et al. Structure-activity studies of irumamycin type macrolides from Streptomyces sp. INA-Ac-5812 // Tetrahedron Letters. 2019. Vol. 60. No. 21. pp. 1448-1451.
GOST all authors (up to 50) Copy
Alferova V. A., Shuvalov M. V., Novikov R. G., Trenin A. S., Dezhenkova L. G., Gladkikh E. G., Lapchinskaya O. A., Kulyaeva V. V., Bychkova O., Mirchink E. P., Solyev P. N., Kudryakova G. K., Korshun V. A., Tyurin A. P. Structure-activity studies of irumamycin type macrolides from Streptomyces sp. INA-Ac-5812 // Tetrahedron Letters. 2019. Vol. 60. No. 21. pp. 1448-1451.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1016/j.tetlet.2019.04.051
UR - https://doi.org/10.1016%2Fj.tetlet.2019.04.051
TI - Structure-activity studies of irumamycin type macrolides from Streptomyces sp. INA-Ac-5812
T2 - Tetrahedron Letters
AU - Alferova, Vera A
AU - Shuvalov, Maxim V
AU - Novikov, Roman G.
AU - Trenin, Alexey S
AU - Dezhenkova, Lubov G
AU - Gladkikh, Elena G
AU - Lapchinskaya, Olda A
AU - Kulyaeva, Valeriya V
AU - Bychkova, Olga
AU - Mirchink, Elena P.
AU - Solyev, Pavel N.
AU - Kudryakova, Gulnara K
AU - Korshun, Vladimir A.
AU - Tyurin, Anton P
PY - 2019
DA - 2019/05/01 00:00:00
PB - Elsevier
SP - 1448-1451
IS - 21
VL - 60
SN - 0040-4039
SN - 1873-3581
ER -
BibTex |
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BibTex Copy
@article{2019_Alferova
author = {Vera A Alferova and Maxim V Shuvalov and Roman G. Novikov and Alexey S Trenin and Lubov G Dezhenkova and Elena G Gladkikh and Olda A Lapchinskaya and Valeriya V Kulyaeva and Olga Bychkova and Elena P. Mirchink and Pavel N. Solyev and Gulnara K Kudryakova and Vladimir A. Korshun and Anton P Tyurin},
title = {Structure-activity studies of irumamycin type macrolides from Streptomyces sp. INA-Ac-5812},
journal = {Tetrahedron Letters},
year = {2019},
volume = {60},
publisher = {Elsevier},
month = {may},
url = {https://doi.org/10.1016%2Fj.tetlet.2019.04.051},
number = {21},
pages = {1448--1451},
doi = {10.1016/j.tetlet.2019.04.051}
}
MLA
Cite this
MLA Copy
Alferova, Vera A., et al. “Structure-activity studies of irumamycin type macrolides from Streptomyces sp. INA-Ac-5812.” Tetrahedron Letters, vol. 60, no. 21, May. 2019, pp. 1448-1451. https://doi.org/10.1016%2Fj.tetlet.2019.04.051.
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