207570-28-3

Upstream product

• 207570-26-1 2-(N-benzyloxycarbonyl-N-methylamino)-3-(3-carbamoylguanidino)propionic acid 
• 207570-25-0 5-(N-benzyloxycarbonyl-N-methylamino)-3,4,5,6-tetrahydro-2-ureidopyrimidin-4-one 
• 14611-34-8 N^α,N^δ,N^ω-tris(benzyloxycarbonyl)-L-arginine 
• 89760-63-4 (S)-1,3-di(benzyloxycarbonyl)-1-(4-benzoyloxycarbonylamino-6-diazo-5-oxohexyl)guanidine 
• 207570-27-2 rac-1,4,5,6-tetrahydro-5-methylamino-2-ureidopyrimidin-4-one 

Downstream Products

• 469905-96-2 TAN1057 

Relevant academic research and scientific papers

Total Synthesis of TAN-1057 A/B, a New Dipeptide Antibiotic from Flexibacter sp. PK-74

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.