469905-96-2Relevant academic research and scientific papers
Total Synthesis of TAN-1057 A/B, a New Dipeptide Antibiotic from Flexibacter sp. PK-74
Sokolov, Viktor V.,Kozhushkov, Sergei I.,Nikolskaya, Sofia,Belov, Vladimir N.,Es-Sayed, Mazen,De Meijere, Armin
, p. 777 - 783 (2007/10/03)
TAN-1057 (1a, b) - a new natural dipeptide antibiotic active against methicillin resistant strains of Staphylococcus aureus - was synthesized starting from Na,Nδ,Nω-tri-Z-L-arginine 20b via the corresponding diazoketone 21b. This upon photolysis rearranged to the ketene which was trapped by (±)-2,4,5,6-tetrahydro-5-methylamino-2-ureidopyrimidin-4-one (3) to yield the fully protected dipeptide 23 (30%). The latter was deprotected by hydrogenolysis to give the final compound as a mixture of two epimers - TAN-1057A, B - isolated previously from a strain of Flexibacter sp. PK-74. The intermediate 3 was prepared from 3-amino-2-(N-Z-N-methylamino)propionic acid methyl ester hydrochloride (16) and 2-methyl-2-thiopseudobiuret hydroiodide (18) in one step in 35% yield.
Total synthesis of the anti methicillin-resistant Staphylococcus aureus peptide antibiotics TAN-1057A-D
Yuan, Chenguang,Williams, Robert M.
, p. 11777 - 11784 (2007/10/03)
TAN-1057A-D, dipeptides isolated from bacteria Flexibacter sp. PK-74 and PK-176, are new antibiotics with potent antibacterial activity against methicillin-resistant Staphylococcus aureus. We describe, in detail, the total synthesis of TAN-1057A-D by a co
