Tetrahedron Letters, volume 60, issue 21, pages 1448-1451
Structure-activity studies of irumamycin type macrolides from Streptomyces sp. INA-Ac-5812
Alferova Vera A
1
,
Shuvalov Maxim V
2
,
Novikov Roman G.
3
,
Trenin Alexey S
1
,
Dezhenkova Lubov G
1
,
Gladkikh Elena G
1
,
Lapchinskaya Olda A
1
,
Kulyaeva Valeriya V
1
,
Bychkova Olga
1
,
Mirchink Elena P.
1
,
Solyev Pavel N.
4
,
Publication type: Journal Article
Publication date: 2019-05-01
Journal:
Tetrahedron Letters
Quartile SCImago
Q3
Quartile WOS
Q3
Impact factor: 1.8
ISSN: 00404039, 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.
Citations by journals
1
|
|
Angewandte Chemie - International Edition
|
Angewandte Chemie - International Edition
1 publication, 14.29%
|
Frontiers in Microbiology
|
Frontiers in Microbiology
1 publication, 14.29%
|
International Journal of Molecular Sciences
|
International Journal of Molecular Sciences
1 publication, 14.29%
|
Angewandte Chemie
|
Angewandte Chemie
1 publication, 14.29%
|
Journal of Natural Products
|
Journal of Natural Products
1 publication, 14.29%
|
Current Topics in Medicinal Chemistry
|
Current Topics in Medicinal Chemistry
1 publication, 14.29%
|
Journal of Infection and Public Health
|
Journal of Infection and Public Health
1 publication, 14.29%
|
1
|
Citations by publishers
1
2
|
|
Wiley
|
Wiley
2 publications, 28.57%
|
Frontiers Media S.A.
|
Frontiers Media S.A.
1 publication, 14.29%
|
Multidisciplinary Digital Publishing Institute (MDPI)
|
Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 14.29%
|
American Chemical Society (ACS)
|
American Chemical Society (ACS)
1 publication, 14.29%
|
Bentham Science
|
Bentham Science
1 publication, 14.29%
|
Elsevier
|
Elsevier
1 publication, 14.29%
|
1
2
|
- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2020,2021,2022,2023,2024],"ids":[0,0,0,0,0],"codes":[0,0,0,0,0],"imageUrls":["","","","",""],"datasets":[{"label":"Citations number","data":[3,2,0,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["42.86","28.57",0,"14.29","14.29"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Angewandte Chemie - International Edition","Frontiers in Microbiology","International Journal of Molecular Sciences","Angewandte Chemie","Journal of Natural Products","Current Topics in Medicinal Chemistry","Journal of Infection and Public Health"],"ids":[19215,24403,14627,25450,16163,3277,19262],"codes":[0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/4QWA67eqfcfyOiA8Wk7YnqroHFqQbTsmDJUYTCTg_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/doUaFUZdxUEQjLi1TwZjGHi8HXYNWWSk04dSC6Xh_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp"],"datasets":[{"label":"","data":[1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[14.29,14.29,14.29,14.29,14.29,14.29,14.29],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["Wiley","Frontiers Media S.A.","Multidisciplinary Digital Publishing Institute (MDPI)","American Chemical Society (ACS)","Bentham Science","Elsevier"],"ids":[11,208,202,40,39,17],"codes":[0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/4QWA67eqfcfyOiA8Wk7YnqroHFqQbTsmDJUYTCTg_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/doUaFUZdxUEQjLi1TwZjGHi8HXYNWWSk04dSC6Xh_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp"],"datasets":[{"label":"","data":[2,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[28.57,14.29,14.29,14.29,14.29,14.29],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Metrics
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
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.
Cite this
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 -
Cite this
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}
}
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.