普罗西米星A - C的全合成及新型呋喃基DNA结合剂的合成。

Total synthesis of proximicin A-C and synthesis of new furan-based DNA binding agents.

作者信息

Wolter Falko E, Schneider Kathrin, Davies Brian P, Socher Elke R, Nicholson Graeme, Seitz Oliver, Süssmuth Roderich D

机构信息

Institut für Chemie, TU Berlin, Strasse des 17. Juni 124, 10623 Berlin, Germany.

出版信息

Org Lett. 2009 Jul 2;11(13):2804-7. doi: 10.1021/ol901003p.

DOI:10.1021/ol901003p

PMID:19552461

Abstract

The total synthesis of the natural occurring polyamides proximicin A-C (3-5) has been accomplished. A short and efficient synthesis of a thus far unknown 4-amino-2-furan carboxylic acid was developed. Furthermore, this unique heterocyclic gamma-amino-acid was used for the synthesis of a new class of AT-selective DNA-binding agents derived from the natural products combining structural features of the proximicins with those from the known DNA-binding natural products netropsin (1) and distamycin (2).

摘要

天然存在的聚酰胺类化合物近霉素A - C（3 - 5）的全合成已完成。开发了一种简短且高效的合成方法来制备一种迄今未知的4 - 氨基 - 2 - 呋喃羧酸。此外，这种独特的杂环γ - 氨基酸被用于合成一类新型的AT选择性DNA结合剂，该类结合剂源自天然产物，结合了近霉素的结构特征与已知的DNA结合天然产物纺锤菌素（1）和偏端霉素（2）的结构特征。