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Sequence-Defined Dithiocarbamate Oligomers via a Scalable, Support-free, Iterative Strategy
Macromolecules ( IF 5.5 ) Pub Date : 2020-12-01 , DOI: 10.1021/acs.macromol.0c00412
Pandurangan Nanjan 1 , Anna Jose 1 , Liya Thurakkal 1 , Mintu Porel 1
Affiliation  

Precise control over the monomeric sequence on natural sequence-defined polymers (SDPs) leads to their structural diversity and functions. However, absolute control over the monomeric sequence on a synthetic polymer remains a challenging process. Herein, we describe a support-free, protection–deprotection-free, cost-effective, and fast iterative strategy for multigram production of a new class of SDP with a unique functional group, dithiocarbamate, a potential group for material and biomedical applications. The strategy is based on a unique monomer, named as amine-hydroxyl monomer, and a three-component reaction between the monomer, CS2, and terminal chloro group of the growing chain. The fast strategy allows us to synthesize a 5-mer sequence-defined oligomer in 6 h. For a proof of concept, a range of aliphatic and aromatic groups have been incorporated at different sequences in the sequence-defined oligomer. This SDP platform has further been advanced by two ways: (i) multiple approaches for postsynthetic modification of SDP and (ii) increasing the chain length in a single step.

中文翻译:

通过可扩展,无支撑,迭代策略的序列定义的二硫代氨基甲酸酯低聚物

精确控制天然序列定义的聚合物(SDP)上的单体序列会导致其结构多样性和功能。然而,对合成聚合物上的单体序列的绝对控制仍然是具有挑战性的过程。本文中,我们描述了一种无支撑,无保护,无脱保护,具有成本效益的快速迭代策略,可以多克生产新型SDP,具有独特的官能团二硫代氨基甲酸酯,这是材料和生物医学应用的潜在基团。该策略基于名为胺-羟基单体的独特单体以及单体CS 2之间的三组分反应,以及增长链的末端氯基。快速策略使我们能够在6小时内合成5聚体序列定义的低聚物。为了进行概念验证,已将一系列脂族和芳族基团以不同的顺序引入序列定义的低聚物中。该SDP平台已通过两种方式进一步改进:(i)SDP的后合成修饰的多种方法,以及(ii)一步增加链长。
更新日期:2020-12-22
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