SYNTHESIS AND CONFORMATIONAL-ANALYSIS OF EPINDOLIDIONE-DERIVED PEPTIDE MODELS FOR BETA-SHEET FORMATION

被引：120

作者：

KEMP, DS

BOWEN, BR

MUENDEL, CC

机构：

[1] Department of Chemistry Room 18-584, Massachusetts Institute of Technology

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 15期

关键词：

D O I：

10.1021/jo00302a033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of 2,8-diaminoepindolidione (2,8-diaminodibenzo[b,g][l,5]naphthyridine-6,12(5,llH)-dione) in 19% yield from p-nitroaniline is reported, as well as further conversion to 2,8-bis(Boc-L-Pro-Xxx)epindolidione (Xxx = Gly, D-Ala) and then to 2,8-bis(OC(Yyy-Zzz-NMe2)-L-Pro-Xxx)epindolidione (Yyy = Gly, L-Ala, D-Ala; Zzz = Gly, L-Phe, D-Phe). The β-turn-forming tendencies of the series 2,8-bis(X-L-Pro-D-Ala)epindolidione, where X “ Ac, Boc, and COGlyOEt, are assigned from XH NMR evidence. © 1990, American Chemical Society. All rights reserved.

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页码：4650 / 4657

页数：8

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