66854-34-0Relevant academic research and scientific papers
Synthesis and Evaluation of Antibacterial Activity of Bottromycins
Yamada, Takeshi,Yagita, Miu,Kobayashi, Yutaka,Sennari, Goh,Shimamura, Hiroyuki,Matsui, Hidehito,Horimatsu, Yuki,Hanaki, Hideaki,Hirose, Tomoyasu,Omura, Satoshi,Sunazuka, Toshiaki
, p. 7135 - 7149 (2018/07/15)
Total synthesis of bottromycin A2 can be accomplished through a diastereoselective Mannich reaction of a chiral sulfinamide, mercury-mediated intermolecular amidination, and cyclization of a constrained tetracyclic peptide. Exploitation of this process allowed the synthesis of several novel bottromycin analogs. The antimicrobial activity of these analogs was evaluated in vitro against Gram-positive bacteria, such as methicillin resistant Staphylococcus aureus (MRSA) and vancomycin resistant enterococci (VRE). Structure-activity relationships were explored taking into consideration the unique three-dimensional structure of the compounds. Notably, one of the new analogs devoid of a methyl ester, which is known to lower the in vivo efficacy of bottromycin, exhibited antibacterial bioactivity comparable to that of vancomycin.
Structure determination and total synthesis of bottromycin A2: A potent antibiotic against MRSA and VRE
Shimamura, Hiroyuki,Gouda, Hiroaki,Nagai, Kenichiro,Hirose, Tomoyasu,Ichioka, Maki,Furuya, Yujiro,Kobayashi, Yutaka,Hirono, Shuichi,Sunazuka, Toshiaki,Omura, Satoshi
supporting information; experimental part, p. 914 - 917 (2009/05/15)
(Chemical Equation Presented) After 50 years of persistence the 12-membered cyclic skeleton of bottromycin A2 (3) has been confirmed by NMR experiments (HMBC), and the configurations of two tLeu residues have been estimated by conformation anal
