Chemical synthesis of 4-azido-β-galactosamine derivatives for inhibitors of N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase

Author:

Hor Seanghai,Kodama Takumi,Sugiura Nobuo,Kondou Hikaru,Yanagida Mio,Yanagisawa Keiya,Shibasawa Aoki,Tsuzuki Bunta,Fukatsu Naoto,Nagao Kazuya,Yamana Kenji,Hidari Kazuya I. P. J.,Watanabe Hideto,Habuchi Osami,Nakano HirofumiORCID

Funder

Joint Usage/Research Center on Tropical Disease, Institute of Tropical Medicine, Nagasaki University

Publisher

Springer Science and Business Media LLC

Subject

Cell Biology,Molecular Biology,Biochemistry

Reference41 articles.

1. Ohtake-Niimi, S., Kondo, S., Ito, T., Kakehi, S., Ohta, T., Habuchi, H., Kimata, K., Habuchi, O.: Mice deficient in N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase are unable to synthesize chondroitin/dermatan sulfate containing N-acetylgalactosamine 4,6-bissulfate residues and exhibit decreased protease activity in bone marrow-derived mast cells. J. Biol. Chem. 285(27), 20793–20805 (2010). https://doi.org/10.1074/jbc.M109.084749

2. Nishimura, K., Ishii, M., Kuraoka, M., Kamimura, K., Maeda, N.: Opposing functions of chondroitin sulfate and heparan sulfate during early neuronal polarization. Neuroscience. 169(4), 1535–1547 (2010). https://doi.org/10.1016/j.neuroscience.2010.06.027

3. Koike, T., Izumikawa, T., Tamura, J., Kitagawa, H.: Chondroitin sulfate-E fine-tunes osteoblast differentiation via ERK1/2, Smad3 and Smad1/5/8 signaling by binding to N-cadherin and cadherin-11. Biochem. Biophys. Res. Commun. 420(3), 523–529 (2012). https://doi.org/10.1016/j.bbrc.2012.03.024

4. Deepa, S.S., Umehara, Y., Higashiyama, S., Itoh, N., Sugahara, K.: Specific molecular interactions of oversulfated chondroitin sulfate E with various heparin-binding growth factors. Implication as physiological binding partner in the brain and other tissues. J. Biol. Chem. 277(46), 43707–43716 (2002). https://doi.org/10.1074/jbc.M207105200

5. Monzavi-Karbssi, B., Stanley, J.S., Hennings, L., Jousheghany, F., Artaud, C., Shaaf, S., Kieber-Emmons, T.: Chondroitin sulfate glycosaminoglycans as major P-selectin ligands on metastatic breast cancer cell lines. Int. J. Cancer. 120(6), 1179–1191 (2007). https://doi.org/10.1002/ijc.22424

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