SYNTHESIS AND CONFORMATIONAL-ANALYSIS OF EPINDOLIDIONE-DERIVED PEPTIDE MODELS FOR BETA-SHEET FORMATION
SYNTHESIS AND CONFORMATIONAL-ANALYSIS OF EPINDOLIDIONE-DERIVED PEPTIDE MODELS FOR BETA-SHEET FORMATION
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DOI：
10.1021/jo00302a033
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发表时间：
1990-07-20
影响因子：
3.6
通讯作者：
MUENDEL, CC
中科院分区：
文献类型：
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作者：
KEMP, DS;BOWEN, BR;MUENDEL, CC
以19%的产率合成了2，8-二氨基二苯并[b，g][1，4]-萘啶-6，12(5，11H)-二酮，并进一步转化为2，8-二(Boc-L-Pro-xxx)-2，8-二(Boc-L-Pro-xxx)二酮(xxx=甘氨酸，D-丙氨酸)，再转化为2，8-bis(OC(Yyy-Zzz-NMe2)-L-Pro-Xxx)epindolidione(yyy=甘氨酸，L-丙氨酸；D-丙氨酸(zzz=甘氨酸，L-Phe，D-Phe))。2，8-双(X-L-Pro-D-Ala)-依吲哚二酮系列化合物的β-转角形成倾向，其中X=Ac，Boc和COGlyOEt，由1H核磁共振证据确定。
Synthesis of 2,8-diaminoepindolidione (2,8-diaminodibenzo[b,g][1,4]naphthyridine-6,12(5,11H)-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 .beta.-turn-forming tendencies of the series 2,8-bis(X-L-Pro-D-Ala)epindolidione, where X = Ac, Boc, and COGlyOEt, are assigned from 1H NMR evidence.