191479-26-2Relevant academic research and scientific papers
Total Synthesis of Tunicamycin v
Yamamoto, Kazuki,Yakushiji, Fumika,Matsumaru, Takanori,Ichikawa, Satoshi
, p. 256 - 259 (2018)
The total synthesis of tunicamycin V is described. This strategy is based on the initial construction of tunicaminyluracil, which is regarded to play an important role in the observed biological activities. The key to the synthesis was a Mukaiyama aldol reaction followed by a furan-oxidation to construct the undecose skeleton, a [3,3] sigmatropic rearrangement of a cyanate, and a highly selective trehalose-type glycosylation.
DPAGT1 Inhibitors of Capuramycin Analogues and Their Antimigratory Activities of Solid Tumors
Mitachi, Katsuhiko,Kansal, Rita G.,Hevener, Kirk E.,Gillman, Cody D.,Hussain, Syed M.,Yun, Hyun Gi,Miranda-Carboni, Gustavo A.,Glazer, Evan S.,Clemons, William M.,Kurosu, Michio
supporting information, p. 10855 - 10878 (2020/11/09)
Capuramycin displays a narrow spectrum of antibacterial activity by targeting bacterial translocase I (MraY). In our program of development of new N-acetylglucosaminephosphotransferase1 (DPAGT1) inhibitors, we have identified that a capuramycin phenoxypiperidinylbenzylamide analogue (CPPB) inhibits DPAGT1 enzyme with an IC50 value of 200 nM. Despite a strong DPAGT1 inhibitory activity, CPPB does not show cytotoxicity against normal cells and a series of cancer cell lines. However, CPPB inhibits migrations of several solid cancers including pancreatic cancers that require high DPAGT1 expression in order for tumor progression. DPAGT1 inhibition by CPPB leads to a reduced expression level of Snail but does not reduce E-cadherin expression level at the IC50 (DPAGT1) concentration. CPPB displays a strong synergistic effect with paclitaxel against growth-inhibitory action of a patient-derived pancreatic adenocarcinoma, PD002: paclitaxel (IC50: 1.25 μM) inhibits growth of PD002 at 0.0024-0.16 μM in combination with 0.10-2.0 μM CPPB (IC50: 35 μM).
A search for pyrophosphate mimics for the development of substrates and inhibitors of glycosyltransferases
Wang, Ruo,Steensma, Darryl H.,Takaoka, Yoshikazu,Yun, Joanne W.,Kajimoto, Tetsuya,Wong, Chi-Huey
, p. 661 - 672 (2007/10/03)
The design and synthesis of several β-1,4-galactosyltransferase inhibitors are reported. Mimics of the pyrophosphate-Mn2+ complex were the focus of the design. Malonic, tartaric, and monosaccharide moieties were used as replacements of the pyrophosphate moiety, and galactose or azasugars with potent galactosidase inhibitory activity were used as the 'donor' component. Compound 6, in which glucose was used as the pyrophosphate-Mn2+ complex mimic and galactose as the 'donor' component, showed the best inhibitory activity towards the transferase with a K(i) of 119.6 μM.
