Heterodetic bicyclic decapeptide cyclo (Glu1-Leu2-Pro3-Gly4-Ser5-Ile6-Pro7- Ala8) cyclo-(1 gamma-5 beta) Phe9-Gly10. Synthesis and 2-D NMR conformational analysis.

G Barbato, G D'Auria, L Paolillo, G Zanotti
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引用次数: 0

Abstract

Bicyclic peptides are useful model molecules that can mimic the constrained local folding of a great number of natural peptides and proteins, such as ionophoric peptides, enzyme active site, and ligand-receptor active site. The synthesis of the bicyclic title compound with the liquid phase method is described with experimental details. Of particular interest is the heterodetic closure of the second ring. The peptide showed a complexing activity with metal cations like Ba2+, Ca2+, and Mg2+. The free bicyclic peptide conformation in solution has been studied by means of NMR spectroscopy and a plausible structure model worked out with model building on NMR constraints is proposed.

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异位双环十肽环(Glu1-Leu2-Pro3-Gly4-Ser5-Ile6-Pro7- Ala8)环-(1 γ -5 β) Phe9-Gly10。合成及二维核磁共振构象分析。
双环肽是一种有用的模型分子,可以模拟许多天然肽和蛋白质的受限局部折叠,如电离层肽、酶活性位点和配体受体活性位点。介绍了液相法合成双环标题化合物的实验细节。特别令人感兴趣的是第二环的异质闭合。该肽具有与Ba2+、Ca2+、Mg2+等金属阳离子络合的活性。利用核磁共振波谱技术研究了溶液中游离双环肽的构象,并在核磁共振约束下建立模型,建立了一个合理的结构模型。
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