首页> 外文期刊>Chemistry: A European journal >Isolation, structure determination, and synthesis of allo-RA-V and neo-RA-V, RA-series bicyclic peptides from Rubia cordifolia L.
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Isolation, structure determination, and synthesis of allo-RA-V and neo-RA-V, RA-series bicyclic peptides from Rubia cordifolia L.

机译:茜草(Rubia cordifolia L)的异源RA-V和neo-RA-V,RA系列双环肽的分离,结构测定和合成。

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Two bicyclic hexapeptides, allo-RA-V (4) and neo-RA-V (5), and one cyclic hexapeptide, O-seco-RA-V (6), were isolated from the roots of Rubia cordifolia L. Their gross structures were elucidated on the basis of spectroscopic analysis and X-ray crystallography of compound 5. The absolute stereochemistry of compounds 4 and 5 were established by their total syntheses, and the absolute stereochemistry of compound 6 by chemical correlation with deoxybouvardin (3). Comparison of the 3D structures of highly active RA-VII (1) with less-active compounds 4 and 5 suggests that the orientation of the Tyr-5 and/or Tyr-6 phenyl rings plays a significant role in their biological activity. The isolation of peptides 4-6, along with compound 3, and the comparison of their structures seem to indicate that peptide 6 may be the common precursor to bicyclic peptides 3-5 in the plant. Allo allo: Two cycloisodityrosine-modified congeners of deoxybouvardin (RA-V) have been isolated from the roots of Rubia cordifolia. Comparison of their structures with that of RA-VII revealed that the orientation of one or both of the Tyr-5 and Tyr-6 phenyl rings plays an essential role in expressing the cytotoxic activity.
机译:从茜草的根中分离出两个双环六肽,即异源RA-V(4)和neo-RA-V(5),和一个环六肽,O-seco-RA-V(6)。通过光谱分析和化合物5的X射线晶体学阐明了化合物的结构。化合物4和5的绝对立体化学是通过它们的总合成建立的,化合物6的绝对立体化学是通过与脱氧布瓦丁的化学相关性确定的(3)。高活性RA-VII(1)与活性较低的化合物4和5的3D结构比较表明,Tyr-5和/或Tyr-6苯环的取向在其生物活性中起重要作用。肽4-6和化合物3的分离以及它们的结构比较似乎表明,肽6可能是植物中双环肽3-5的常见前体。 Allo allo(同种异体):已从茜草的根中分离出两个环氧异丁烷修饰的脱氧布瓦丁(RA-V)同系物。它们的结构与RA-VII的结构比较表明,Tyr-5和Tyr-6苯环之一或二者的取向在表达细胞毒性活性中起着重要作用。

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