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塞洛京汀C右手环的合成。

Synthesis of the celogentin C right-hand ring.

作者信息

He Liwen, Yang Liping, Castle Steven L

机构信息

Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, USA.

出版信息

Org Lett. 2006 Mar 16;8(6):1165-8. doi: 10.1021/ol060016f.

Abstract

[reaction: see text] Synthesis of the cyclic tetrapeptide comprising the right-hand ring of celogentin C, a potent inhibitor of tubulin polymerization, has been accomplished. A mild oxidative coupling reaction permitted construction of the indole-imidazole linkage via a convergent union of two fully functionalized dipeptides. A high-yielding macrolactamization and subsequent deprotection of the N-terminus furnished the target compound.

摘要

[反应:见正文] 已完成包含塞洛金汀C右手环的环四肽的合成,塞洛金汀C是一种有效的微管蛋白聚合抑制剂。温和的氧化偶联反应通过两个完全功能化的二肽的汇聚结合构建了吲哚 - 咪唑键。高产率的大环内酰胺化反应以及随后N端的脱保护得到了目标化合物。

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本文引用的文献

1
Asymmetric synthesis of the central tryptophan residue of stephanotic acid.
Org Biomol Chem. 2004 Dec 21;2(24):3545-7. doi: 10.1039/b414996c. Epub 2004 Nov 3.
2
Catalytic asymmetric synthesis of the central tryptophan residue of celogentin C.
Org Lett. 2003 Oct 2;5(20):3611-4. doi: 10.1021/ol035236x.
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Celogentins A-C, new antimitotic bicyclic peptides from the seeds of Celosia argentea.
J Org Chem. 2001 Oct 5;66(20):6626-33. doi: 10.1021/jo0103423.
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Antimitotic activity of moroidin, a bicyclic peptide from the seeds of Celosia argentea.
Bioorg Med Chem Lett. 2000 Mar 6;10(5):469-71. doi: 10.1016/s0960-894x(00)00029-9.

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