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Synthesis of a Chloroalkene Dipeptide Isostere-Containing Peptidomimetic and Its Biological Application
ACS Medicinal Chemistry Letters ( IF 3.5 ) Pub Date : 2018-01-02 00:00:00 , DOI: 10.1021/acsmedchemlett.7b00234 Takuya Kobayakawa 1 , Yudai Matsuzaki 1 , Kentaro Hozumi 2 , Wataru Nomura 1 , Motoyoshi Nomizu 2 , Hirokazu Tamamura 1
ACS Medicinal Chemistry Letters ( IF 3.5 ) Pub Date : 2018-01-02 00:00:00 , DOI: 10.1021/acsmedchemlett.7b00234 Takuya Kobayakawa 1 , Yudai Matsuzaki 1 , Kentaro Hozumi 2 , Wataru Nomura 1 , Motoyoshi Nomizu 2 , Hirokazu Tamamura 1
Affiliation
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The first rapid and efficient chemical synthesis of a cyclic Arg-Gly-Asp (RGD) peptide containing a chloroalkene dipeptide isostere (CADI) is reported. By a developed synthetic method, an N-tert-butylsulfonyl protected CADI was obtained utilizing diastereoselective allylic alkylation as a key reaction. This CADI was also transformed into an N-Fmoc protected CADI in a few steps. The CADI was used in Fmoc-based solid-phase peptide synthesis. The first synthesis of a CADI-containing cyclic RGD peptide was successful, and the synthesized CADI-containing peptidomimetic was found to be a more potent inhibitor against integrin-mediated cell attachment than the parent cyclic peptide.
中文翻译：
含氯烯二肽等排异构体的拟肽的合成及其生物学应用
据报道，首次快速，有效地化学合成了包含氯烯二肽等排物（CADI）的环状Arg-Gly-Asp（RGD）肽。由发达合成法，ñ -叔-butylsulfonyl保护得到CADI利用非对映选择性烯丙基烷基化作为关键反应。只需几个步骤，该CADI也已转换为N- Fmoc保护的CADI。CADI用于基于Fmoc的固相肽合成中。含CADI的环状RGD肽的首次合成成功，并且发现所合成的含CADI的拟肽比亲本环状肽对整合素介导的细胞附着的抑制作用更强。
更新日期：2018-01-02
中文翻译：
含氯烯二肽等排异构体的拟肽的合成及其生物学应用
据报道，首次快速，有效地化学合成了包含氯烯二肽等排物（CADI）的环状Arg-Gly-Asp（RGD）肽。由发达合成法，ñ -叔-butylsulfonyl保护得到CADI利用非对映选择性烯丙基烷基化作为关键反应。只需几个步骤，该CADI也已转换为N- Fmoc保护的CADI。CADI用于基于Fmoc的固相肽合成中。含CADI的环状RGD肽的首次合成成功，并且发现所合成的含CADI的拟肽比亲本环状肽对整合素介导的细胞附着的抑制作用更强。
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