Stereochemistry of kahalalide F
Stereochemistry of kahalalide F
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DOI：
10.1021/np030334c
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发表时间：
2003-11-01
影响因子：
5.1
通讯作者：
Rinehart, KL
中科院分区：
文献类型：
--
作者：
Bonnard, I;Manzanares, I;Rinehart, KL
在海洋衍生的环状缩酚酸肽kahalalide F中的氨基酸的立体化学已经通过一系列降解反应（水解、臭氧分解、Edman降解、和Marvinyl衍生化）来定义，产生海洋天然产物的较小片段。这些反应的结果与最初由Hamann和Scheuer提出的结构一致，并且与最近由Goetz，Yoshida和Scheuer提出的大多数组分氨基酸的立体化学相同。然而，我们对D-Val（3）和L-Val（4）的赋值与以前对L-Val（3）和D-Val（4）的赋值相反。目前（反向）立体化学是至关重要的抗肿瘤活性的kahalalide F。
The stereochemistry of the amino acids in the marine-derived cyclic depsipeptide kahalalide F has been defined by a series of degradation reactions (hydrolysis, ozonolysis, Edman degradation, and Marfey derivatization), yielding smaller fragments of the marine natural product. The results from these reactions agree with the structure originally proposed by Hamann and Scheuer and with the same stereochemistry of most of the component amino acids more recently proposed by Goetz, Yoshida, and Scheuer. However, our assignments Of D-Val(3) and L-Val(4) are the reverse of previous assignments made as L-Val(3) and D-Val(4). The present (reversed) stereochemistry is crucial for the antitumor activity of kahalalide F.