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Total Syntheses and Biological Activities of Vinylamycin Analogues.
Wang J, Kuang B, Guo X, Liu J, Ding Y, Li J, Jiang S, Liu Y, Bai F, Li L, Zhang Q, Zhu XY, Xia B, Li CQ, Wang L, Yang G, Chen Y. Wang J, et al. J Med Chem. 2017 Feb 9;60(3):1189-1209. doi: 10.1021/acs.jmedchem.6b01745. Epub 2017 Jan 20. J Med Chem. 2017. PMID: 28075592
Natural depsipeptide vinylamycin was reported to be an antibiotic previously. Herein we report vinylamycin to be active against K562 leukemia cells (IC(50) = 4.86 muM) and be unstable in plasma (t(1/2) = 0.54 h). A total of 24 vinylamycin analogues with modif …
Natural depsipeptide vinylamycin was reported to be an antibiotic previously. Herein we report vinylamycin to be active agains …
Vinylamycin, a new depsipeptide antibiotic, from Streptomyces sp.
Igarashi M, Shida T, Sasaki Y, Kinoshita N, Naganawa H, Hamada M, Takeuchi T. Igarashi M, et al. J Antibiot (Tokyo). 1999 Oct;52(10):873-9. doi: 10.7164/antibiotics.52.873. J Antibiot (Tokyo). 1999. PMID: 10604756 Free article.
Vinylamycin was isolated from the culture broth by extraction with EtOAc and purified by crystallization from EtOAc. The structure of vinylamycin was determined by spectroscopic analysis and degradation studies. Vinylamycin showed antimicrobial activities aga …
Vinylamycin was isolated from the culture broth by extraction with EtOAc and purified by crystallization from EtOAc. The structure of …
Total Synthesis and Determination of the Absolute Configuration of Vinylamycin.
Yang Z, Yang G, Ma M, Li J, Liu J, Wang J, Jiang S, Zhang Q, Chen Y. Yang Z, et al. Org Lett. 2015 Dec 4;17(23):5725-7. doi: 10.1021/acs.orglett.5b02809. Epub 2015 Nov 2. Org Lett. 2015. PMID: 26523486
The absolute configurations of the three unknown chiral centers in vinylamycin were predicted according to the structural comparison with microtermolide A and rakicidin A, and then total syntheses of vinylamycin were applied to determine the three unknown chiral cen …
The absolute configurations of the three unknown chiral centers in vinylamycin were predicted according to the structural comparison …
Microtermolides A and B from termite-associated Streptomyces sp. and structural revision of vinylamycin.
Carr G, Poulsen M, Klassen JL, Hou Y, Wyche TP, Bugni TS, Currie CR, Clardy J. Carr G, et al. Org Lett. 2012 Jun 1;14(11):2822-5. doi: 10.1021/ol301043p. Epub 2012 May 16. Org Lett. 2012. PMID: 22591554 Free PMC article.
Structural elucidation of 1 led to the re-examination of the structure originally proposed for vinylamycin (3). Based on a comparison of predicted and experimental (1)H and (13)C NMR chemical shifts, we propose that vinylamycin's structure be revised from 3 to 4....
Structural elucidation of 1 led to the re-examination of the structure originally proposed for vinylamycin (3). Based on a comparison …
Determination of the Absolute Configurations of Microtermolides A and B.
Yang Z, Ma M, Yang CH, Gao Y, Zhang Q, Chen Y. Yang Z, et al. J Nat Prod. 2016 Sep 23;79(9):2408-12. doi: 10.1021/acs.jnatprod.5b01143. Epub 2016 Aug 31. J Nat Prod. 2016. PMID: 27579840
However, on the basis of a structural comparison with vinylamycin, another depsipeptide with a unique 4-amino-2,4-pentadienolate structure, the chiral centers could also be assigned as 2R, 3R, and 4S. ...
However, on the basis of a structural comparison with vinylamycin, another depsipeptide with a unique 4-amino-2,4-pentadienolate stru …
Total synthesis and determination of the absolute configuration of rakicidin A.
Sang F, Li D, Sun X, Cao X, Wang L, Sun J, Sun B, Wu L, Yang G, Chu X, Wang J, Dong C, Geng Y, Jiang H, Long H, Chen S, Wang G, Zhang S, Zhang Q, Chen Y. Sang F, et al. J Am Chem Soc. 2014 Nov 5;136(44):15787-91. doi: 10.1021/ja509379j. Epub 2014 Oct 24. J Am Chem Soc. 2014. PMID: 25286338
This work suggests strategies for the determination of unknown chiral centers in other cyclic depsipeptides, such as rakicidin B, C, D, BE-43547, and vinylamycin, and facilitates the investigations of rakicidin A as an anticancer stem cell agent....
This work suggests strategies for the determination of unknown chiral centers in other cyclic depsipeptides, such as rakicidin B, C, D, BE-4 …