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首页> 外文会议>American Peptide Symposium >O-Acyl Isopeptide Method: Toward an Efficient Chemical Preparation of Peptides/Proteins Using Racemization-Free Segment Condensation Method
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O-Acyl Isopeptide Method: Toward an Efficient Chemical Preparation of Peptides/Proteins Using Racemization-Free Segment Condensation Method

机译：O-酰基异肽法：使用无条件的段冷凝法朝向肽/蛋白质的有效化学制备

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Pcptides and proteins synthesized by chemical means have been widely used in biological studies To synthesize longer peptides and proteins, many kinds of convergent synthetic methods have been proposed. Among them, "segment condensation", in which a side-chain protected peptide carboxylate is coupled with an amino group of another peptide segment to construct a longer peptide, has attracted attention as an important method. However, a fundamental drawback of the segment condensation is that epimerization at the C-terminal residue. of an N-segment occurs during the condensation reaction with a C-segment (Figure 1A), limiting the N-segment to contain either a C-terminal Gly or Pro. This epimerization occurs because, in contrast to urethane-protected amino acids, peptides easily form chirally labile oxazolones upon C-terminal carboxyl activation. Recently, we have developed "racemization-free segment condensation" based on the O-acyl isopeptide method (Figure 1) [1]. The idea was that an N-segment with a C-terminal isopeptide structure (O-acyl Ser/Thr residue) can be coupled to an N-terminal amino group of the. C-segment without any epimerization, because the amino group of C-terminal isopeptide part is protected by a urethane-type protective group [2]. Activation of the carboxyl group of the isopeptide ide was thus expected to suppress the formation of racemization-inducing oxazolone. Toward future protein synthesis, we herein synthesized bioactive peptides by the O-acyl isopeptide method-based racemization-free segment condensation method.
机译：通过化学方法合成的PCPTIDES和蛋白质已广泛用于生物学研究中以合成较长的肽和蛋白质，已经提出了许多种种会聚的合成方法。其中，“分段缩合”，其中侧链受保护的肽羧酸盐与另一个肽区段的氨基偶联以构建较长的肽，引起了关注作为一种重要的方法。然而，分段缩合的基本缺点是C末端残留物的差异。在与C段（图1a）的缩合反应期间发生n段（图1a），限制n段含有C末端Gly或Pro。发生这种差异，因为与氨基甲酸酯保护的氨基酸相反，肽在C末端羧基活化时容易形成手性不稳定恶唑酮。最近，我们基于O-酰基异肽法（图1）[1]开发了“无条纹段冷凝”。该想法是具有C末端异肽结构（O-酰基SER / THR残基）的N段可以与N-末端氨基偶联。 C段没有任何差异，因为C末端异肽部分的氨基受氨基甲酸酯型保护基的保护[2]。因此预期异肽IDE的羧基的活化抑制了诱导诱导恶唑酮的形成。对于未来的蛋白质合成，我们在本文中由基于O-酰基异肽法的无条状的基于外消除段冷凝方法合成的生物活性肽。

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