86807-93-4

Upstream product

• 186581-53-3 diazomethane 
• 51219-19-3 N^α-tert-butoxycarbonyl-N^δ,N^ω-di-benzyloxycarbonyl-L-arginine 

Downstream Products

• 775534-55-9 C₂₃H₂₇ClN₄O₅ 
• 198416-21-6 C₄₂H₅₁N₉O₁₁ 
• 198416-17-0 C₄₄H₅₄N₆O₁₁ 

Relevant academic research and scientific papers

Potent bivalent thrombin inhibitors: Replacement of the scissile peptide bond at P1-P1' with arginyl ketomethylene isosteres

We have designed highly potent synthetic bivalent thrombin inhibitors, which consist of an active site blocking segment, a fibrinogen recognition exosite blocking segment, and a linker connecting these segments. The bivalent inhibitors bind to the active

Exploring the Sn binding pockets in gingipains by newly developed inhibitors: Structure-based design, chemistry, and activity

Arg-gingipains (Rgps) and Lys-gingipain (Kgp) are cysteine proteinases secreted by Porphyromonas gingivalis, the major pathogen implicated in periodontal disease. Gingipains are essential to the bacterium for its virulence and survival, and development of inhibitors targeting these proteins provides an approach to treat periodontal diseases. Here, we present the first example of structure-based design of gingipains inhibitors, with the use of the crystal structure of RgpB and the homology model of Kgp. Chloromethyl ketones were selected as suitable compounds to explore the specificity of the Sn binding region of both enzymes. Three series of inhibitors bearing Arg or Lys at P1 and different substituents at P2 and P3 were designed, synthesized, and tested. High potency (kobs/[I] ～ 107 M-1 s -1) was achieved for small ligands, such as the dipeptide analogues. The detailed analysis of Sn binding pockets revealed the molecular basis of inhibitory affinity and provided insight into the structure-activity relationship.

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.

Total synthesis of the anti methicillin-resistant Staphylococcus aureus peptide antibiotics TAN-1057A-D

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

Tripeptidyl pyridinium methyl ketones as potent active site inhibitors of thrombin

Several substituted methyl ketone derivatives of tripeptides with a C-terminal arginyl residue were synthesized as active site inhibitors of human α-thrombin. The most active compound among this series was the pyridinium methyl ketone D-Cha-Pro-Arg-PMK, w

A facile conversion of arginine into β-homoarginine dipeptides

Irradiation of the arginine derived diazomethyl ketone 2 in the presence of amino esters gives the corresponding β-homoarginine dipeptide esters 3c-h in 45-76 % yield.