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首页> 外文期刊>Chemistry: A European journal >Synthesis of Conformationally Restricted Mimetics of #gamma#-Turns and Incorporation into Desmopressin, an Analogue of the Peptide Hormone Vasopressin
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Synthesis of Conformationally Restricted Mimetics of #gamma#-Turns and Incorporation into Desmopressin, an Analogue of the Peptide Hormone Vasopressin

机译：合成限制构象的＃γ＃-Turns模拟物并掺入去氨加压素中，去氨加压素是肽激素加压素的类似物。

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摘要

Mimetics of tripeptides adopting inverse and classical #gamma#-turn conformations have been designed adn synthesized by an enantioselective approach and then incorporated in an analogue of the hormone vasopressin. In the mimetics one of the amide bonds of the #gamma#-turn has been exchanged for a #PSI#[CH_2O] isostere and the hydrogen bond between residues i and i+2 of the turn has been replaced by a methylene bridge to give a six-membered, morpholin-3-one ring. The turn mimetics were assembled from three types of building blocks: azido epoxides, #alpha#-bromo acids and #beta#-amino alcohols. Of these, the stereochemistry of the azido epoxide determines whether a classical or an inverse #gamma#-turn is mimicked. The key azido epoxide building blocks were preparedin six steps and approximately 40% overall yield, whereas the #alpha#-bromo acids and #beta#-amino alcohols were either commercially available or readily prepared from amino acids. The building block approach allowed substantial variation of the side chains of the mimetics, together with complete stereocontrol, as well as use of uniform conditions for preparation of both classical and inverse #gamma#-turn mimetics. Conformational studies based on ab initio calculations and ~1H NMR spectroscopy revealed that the minimum-energy conformations of the mimetics closely resembled inverse or classical #gamma#-turns.
机译：已经采用对映选择性的方法设计和合成了采用逆向和经典的＃γ＃-转角构象的三肽模拟物，然后将其掺入激素加压素的类似物中。在模拟物中，已将＃γ＃转的酰胺键中的一个交换为＃PSI＃[CH_2O]等位异构体，并将转弯的残基i和i + 2之间的氢键替换为亚甲基桥，得到六元吗啉-3-一环转弯模拟物由三种类型的构件组装而成：叠氮基环氧化物，＃α＃-溴酸和＃β＃-氨基醇。其中，叠氮基环氧化合物的立体化学决定了是模仿经典的还是反向的＃γ＃转角。关键的叠氮基环氧化合物的构建步骤分六个步骤，总收率约为40％，而＃alpha＃-溴酸和＃beta＃-氨基醇可商购或从氨基酸容易制备。构造方法允许模拟物的侧链发生实质性变化，以及完全的立体控制，以及使用统一的条件来制备经典和逆向的＃gamma＃转弯模拟物。根据从头算和1H NMR光谱学进行的构象研究表明，模拟物的最小能量构象与逆向或经典的＃γ＃匝数极为相似。

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