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采用硫内酯化学的序列定义的寡尿烷酰胺的自动化合成方案。

Automated Synthesis Protocol of Sequence-Defined Oligo-Urethane-Amides Using Thiolactone Chemistry.

机构信息

Polymer Chemistry Research Group, Centre of Macromolecular Chemistry, Department of Organic and Macromolecular Chemistry, Faculty of Sciences, Ghent University, Krijgslaan 281 S4-bis, B-9000, Ghent, Belgium.

Institut Charles Sadron, CNRS, Université de Strasbourg, F-67000, Strasbourg, France.

出版信息

Macromol Rapid Commun. 2019 Jan;40(1):e1800685. doi: 10.1002/marc.201800685. Epub 2018 Nov 19.

DOI:10.1002/marc.201800685
PMID:30456847
Abstract

An automated, iterative protocol for the synthesis of multifunctional, sequence-defined oligo-urethane-amides using thiolactone chemistry is reported. Here, sequenced functionalization of the backbone is easily introduced using commercially available primary amines. The chemistry is carried out on solid phase using different supports for better optimization of the synthetic protocol and in order to demonstrate the versatility of the approach. This technique is very effective for iterative synthesis and solid-phase chemistry and enables the exploration of full automation of this approach using a robotic peptide synthesizer. As a result, this automated protocol allows for the synthesis of a sequence-defined nonamer of high purity.

摘要

本文报道了一种使用硫内酯化学合成多功能、序列定义的寡聚氨酯酰胺的自动化、迭代合成方案。在这里,使用商业上可用的伯胺很容易引入对主链的序列功能化。该化学方法在固相上进行,使用不同的载体以更好地优化合成方案,并展示该方法的多功能性。该技术对于迭代合成和固相化学非常有效,并能够使用机器人肽合成器探索该方法的完全自动化。结果,该自动化方案允许合成高纯度的序列定义的九聚体。

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