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1 pp. Peptidomimetic-based medicinal chemistry Tetsuo Narumi and Hirokazu Tamamura Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, Kandasurugadai, Chiyoda-ku, Tokyo, Japan ground state mimetic transition state mimetic
2 anti-sn CXCR FC CXCR G CXCL EADI E TADI E FADI Z CF -ADI Z SDF- HIV CXCR FC nm CXCR FC Arg-Arg Arg-Nal Nal-Gly CXCR FC Arg- Arg Nal-Gly CXCR Arg-Nal Arg-Nal Arg-Nal N-H α- γ- S-S B - - -Asp-Thr Ser -Gly- HIV β- γ-
3 A FC FC nm CXCRFC FC B FC FC hydroxyethylamine dipeptide isostere HDI HDI HIV TYA TYB TYA TYB saquinavir Roche nelfinavir Pfizer amprenavir Vertex HIV TYA TYA HIV P -P TYB TYB HIV HIV β-
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6 β Aββ APP β- γ- β- protein-tyrosine kinase PTK protein-tyrosine phosphatase PTP PTK SH fos jun PTK PTP PTK PTP ptyr Pmp ptyr pka F Pmp ptyr ptyr Burke Otaka HIV CD HIV CD CCR CXCR HIV CD HIV gp gp-cd - HIV gp NBD- HIV- HIV Kd µm NBD- CD gp gp CD CD gp CD Phe gp Phe- cavity CD gp Flex-SIS module of SYBYL Phe Arg gp NBD- Phe Arg gp NBD- CD Phe- cavity A gp Trp Phe Trp gp CD CD
7 HIV A CD HIV gp B gp-cd - C gp D HR NHR, N-region HR CHR, C-region A NBD-B gp CD PDB entry RZJ C gp NBD- Flex-SIS module of SYBYL D gp NBD- Phe- cavity NBD- HIV gp CCR CXCR
8 C HIV gp HIV gp N HR NHR N-region C HR CHR C-region HIV gp-cd - gp HR HR Enfurvirtide Roche Enfurvirtide HR CHR C-region HR HR HR HR HIV HIV gp F E gp gp gp HR HR gp gp gp C HR NHR N-region N gpn N CD α C A HR NHR N-region N N B C N HR CHR C-region C α gp N ELIZA N N N N N C
9 Hann, M.M. & Sammes, P.G.J. Chem. Soc., Perkin Trans.,. Oishi, S., Kamano, T., Niida, A., Odagaki, Y., Hamanaka, N., Yamamoto, M., Ajito, K., Tamamura, H., Otaka, A., & Fujii, N.J. Org. Chem.,,. Abraham, R.J., Ellison, S.L.R., Schonholzer, P., & Thomas, W. A.Tetrahedron,,. Wipf, P., Henninger, T.C., & Geib, S.J.J. Org. Chem.,,. Bondi, A.J. Phys. Chem.,,. Ibuka, T., Habashita, H., Funakoshi, S., Fujii, N., Oguchi, Y., Uyehara, T., & Yamamoto, Y.Angew, Chem. Int. Ed. Engl.,,. Narumi, T., Niida, A., Tomita, K., Oishi, S., Otaka, A., Ohno, H., & Fujii, N.Chem. Commun.,. Tamamura, H. & Fujii, N.Expert Opin. Ther. Targets,,. Fujii, N., Oishi, S., Hiramatsu, K., Araki, T., Ueda, S., Tamamura, H., Otaka, A., Kusano, S., Terakubo, S., Nakashima, H., Broach, J.A., Trent, J.O., Wang, Z., & Peiper, S.C. Angew, Chem. Int. Ed. Engl.,,. Tamamura, H., Hiramatsu, K., Ueda, S., Wang, Z., Kusano, S., Terakubo, S., Trent, J.O., Peper, S.C., Yamamoto, N., Nakashima, H., Otaka, A., & Fujii, N.J. Med. Chem.,,. Narumi, T., Hayashi, R., Tomita, K., Kobayashi, K., Tanahara, N., Ohno, H., Naito, T., Kodama, E., Matsuoka, M., Oishi, S., & Fujii, N.Org. Biomol. Chem.,,. Tamamura, H., Araki, T., Ueda, S., Wang, Z., Oishi, S., Esaka, A., Trent, J.O., Nakashima, H., Yamamoto, N., Peiper, S.C., Otaka, A., & Fujii, N.J. Med. Chem.,,. Bursavich, M.G. & Rich, D.H.J. Med. Chem.,,. Tamamura, H., Hori, T., Otaka, A., & Fujii, N.J. Chem. Soc., Perkin Trans.,,. Tamamura, H., Koh, Y., Ueda, S., Sasaki, Y., Yamasaki, T., Aoki, M., Maeda, K., Watai, Y., Arikuni, H., Otaka, A., Mitsuya, H., & Fujii, N.J. Med. Chem.,,. Tamamaura, H., Kato, T., Otaka, A., & Fujii, N.Org. Biomol. Chem.,,. pp. Burke, T.R., Yao, Z.J., Smyth, M.S., & Ye, B.Curr. Pharm. Design,,. Otaka, A., Miyoshi, K., Kaneko, M., Tamamura, H., Fujii, N., Nomizu, M., Burke, T.R., & Roller, P.P.J. Org. Chem.,,. Chan, D.C. & Kim, P.S.Cell,,. Zhao,Q.,Ma,L.,Jang,S.,Lu,H.,Liu,S.,He,Y.,Strick,N., Neamati, N., & Debnath, A.K.Virology,,. Mandai, N., Schön, A., Princiotto, A.M., LaLonde, J.M., Courter, J.R., Soeta, T., Ng, D., Wang, L., Brower, E.T., Xiang, S.-H., Kwon, Y.D., Huang, C.-C., Wyatt, R., Kwong, P. D., Freire, E., Smith III, A.B., & Sodroski, J.Structure,,. Yamada, Y., Ochiai, C., Yoshimura, K., Tanaka, T., Ohashi, N., Narumi, T., Nomura, W., Harada, S., Matsushita, S., & Tamamura, H.Bioorg. Med. Chem. Lett.,,. Lu, M., Blacklow, S.C., & Kim, P.S.Nat. Struct. Biol.,,. Lu,M.&Kim,P.S.J. Biomol. Struct. Dyn.,,. Wild, C., Greenwell, T., & Matthews, T.AIDS Res. Hum. Retroviruses,, Weiss, C.D.AIDS Rev.,,. Alam, S.M., McAdams, M., Boren, D., Rak, M., Scearce, R. M., Gao, F., Camacho, Z.T., Gewirth, D., Kelsoe, G., Chen, P. J., & Haynes, B.F.J. Immunol.,,. Otaka, A., Nakamura, M., Nameki, D., Kodama, E., Uchiyama, S., Nakamura, S., Nakano, H., Tamamura, H., Kobayashi, Y., Matsuoka, M., & Fujii, N.Angew. Chem. Int. Ed. Engl.,,. Tam, J.P. & Yu, Q.Org. Lett.,,. Louis, J.M., Nesheiwat, I., Chang, L., Clore, G.M., & Bewlet, C.A.J. Biol. Chem.,,. Xu, W. & Taylor, J.W.Chem. Biol. Druf. Des.,,. Nakahara, T., Nomura, W., Ohba, K., Ohya, A., Tanaka, T., Hashimoto, C., Narumi, T., Murakami, T., Yamamoto, N., & Tamamura, H.Bioconjugate Chem.,,.
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