Studies on intramolecular hydrogen bonding between the pyridine nitrogen and the amide hydrogen of the peptide: synthesis and conformational analysis of tripeptides containing novel amino acids with a pyridine ring
Studies on intramolecular hydrogen bonding between the pyridine nitrogen and the amide hydrogen of the peptide: synthesis and conformational analysis of tripeptides containing novel amino acids with a pyridine ring
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DOI：
10.1002/psc.647
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发表时间：
2005-07-01
影响因子：
2.1
通讯作者：
Yamada, T
中科院分区：
文献类型：
--
作者：
Hanyu, M;Ninomiya, D;Yamada, T
采用固相Ugi反应首次制备了含有α -甲基- α -（2-吡啶基）甘氨酸（2Pmg）和α -（2-吡啶基）甘氨酸（2Pyg）的Z-AA(1)-Xaa-AA(3)- ome (AA（1)和AA(3) = Gly或Aib， Xaa = 2Pmg和2Pyg）三肽。这些结果清楚地表明，固相Ugi反应对于制备含有吡啶环的氨基酸的三肽是非常有用的。核磁共振分析表明，含2mg - nh的三肽具有独特的构象，2mg - nh与吡啶氮之间存在分子内氢键。然而，在Z-Gly-Pyg-Gly-Me中，没有观察到2Pyg-NH与吡啶氮之间的分子内氢键，而Z-Aib-2Pyg-Aib-OMe采用独特的构象，2Pyg-NH与吡啶氮之间存在分子内氢键。构象分析的三肽,Z-AA (1) -Xaa-AA (3) - ome (AA AA (1), (3) = g或爱尔兰联合银行,Xaa =α,alpha-di (2-pyridyl)甘氨酸(2 dpy), alpha-phenyl-alpha——(2-pyridyl)甘氨酸(2分),2体和2 pyg),澄清说,当一个α,alpha-disubstituted甘氨酸与2-pyridyl集团在一个α碳原子引入任何肽,吡啶氮之间的分子内氢键和酰胺质子和构象流动形成的肽是支柱。限制。版权所有(c) 2005欧洲多肽协会和约翰威利父子有限公司
For the first time tripeptides, Z-AA(1)-Xaa-AA(3)-OMe (AA(1) and AA(3) = Gly or Aib, Xaa = 2Pmg and 2Pyg) were prepared containing alpha-methyl-alpha-(2-pyridyl)glycine (2Pmg) and alpha-(2-pyridyl)glycine (2Pyg) by solid-phase Ugi reaction. These results clearly indicate that for the preparation of tripeptides containing an amino acid with a pyridine ring, the solid-phase Ugi reaction is very useful. NMR analysis clarified that 2Pmg-containing tripeptides adopt a unique conformation with an intramolecular hydrogen bond between 2Pmg-NH and the pyridine nitrogen. However, in the case of Z-Gly-Pyg-Gly-Me, the intramolecular hydrogen bonding between 2Pyg-NH and the pyridine nitrogen was not observed, whereas Z-Aib-2Pyg-Aib-OMe adopts a unique conformation with an intramolecular hydrogen bond between 2Pyg-NH and a pyridine nitrogen. Conformational analysis of the tripeptides, Z-AA(1)-Xaa-AA(3)-OMe (AA(1), AA(3) = Gly or Aib, Xaa = alpha,alpha-di(2-pyridyl)glycine (2Dpy), alpha-phenyl-alpha-(2-pyridyl)glycine (2Ppg), 2Pmg and 2Pyg), clarified that when an alpha,alpha-disubstituted glycine with a 2-pyridyl group at an alpha-carbon atom is introduced into any peptide, an intramolecular hydrogen bond between a pyridine nitrogen and an amide proton is formed and conformational mobility of the peptide backbone is. restricted. Copyright (c) 2005 European Peptide Society and John Wiley & Sons, Ltd.