New Aldehyde-Functional Methacrylic Water-Soluble Polymers.
New Aldehyde-Functional Methacrylic Water-Soluble Polymers.
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DOI：
10.1002/anie.202015298
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发表时间：
2021-05-17
期刊：
影响因子：
--
通讯作者：
Armes SP
中科院分区：
文献类型：
--
作者：
Brotherton EE;Jesson CP;Warren NJ;Smallridge MJ;Armes SP
醛基团使得能够容易地缀合至蛋白质、酶、寡核苷酸或荧光染料，但是没有水溶性醛官能化乙烯基单体的文献实例。我们报道了一种新的亲水性顺式二醇基甲基丙烯酸酯单体（GEO 5 MA）的合成，其通过使用甲基丙烯酸甲酯的异亚丙基甘油五（乙二醇）的酯交换反应，然后通过酸水解进行丙酮脱保护。相应的水溶性醛单体AGE 05 MA通过GEO 5 MA在22 °C下的水性高碘酸盐氧化制备。GEO 5 MA的RAFT聚合产生水溶性均聚物PGEO 5 MA。在22 °C下，PGEO 5 MA上的末端顺式二醇单元的水性高碘酸盐氧化得到水溶性醛官能均聚物（PAGE 05 MA）。此外，使用亚化学计量的高碘酸盐/顺式二醇摩尔比制备具有顺式二醇和醛基的亲水性统计共聚物库。PAGE 0 5 MA均聚物上的醛基依次与三种氨基酸反应以证明合成效用。通过在22 °C下氧化GEO 5 MA来制备水溶性醛单体（AGEO 5 MA）。RAFT水性聚合产生PAGE 0 5 MA均聚物，使用亚化学计量的高碘酸盐/顺式二醇摩尔比将其氧化以产生具有顺式二醇和醛基的亲水性统计共聚物。将三种基于PGEO 5 MA的二嵌段共聚物转化为醛官能共聚物，其用氨基酸衍生化。
Aldehyde groups enable facile conjugation to proteins, enzymes, oligonucleotides or fluorescent dyes, yet there are no literature examples of water‐soluble aldehyde‐functional vinyl monomers. We report the synthesis of a new hydrophilic cis‐diol‐based methacrylic monomer (GEO5MA) by transesterification of isopropylideneglycerol penta(ethylene glycol) using methyl methacrylate followed by acetone deprotection via acid hydrolysis. The corresponding water‐soluble aldehyde monomer, AGEO5MA, is prepared by aqueous periodate oxidation of GEO5MA at 22 °C. RAFT polymerization of GEO5MA yields the water‐soluble homopolymer, PGEO5MA. Aqueous periodate oxidation of the terminal cis‐diol units on PGEO5MA at 22 °C affords a water‐soluble aldehyde‐functional homopolymer (PAGEO5MA). Moreover, a library of hydrophilic statistical copolymers bearing cis‐diol and aldehyde groups was prepared using sub‐stoichiometric periodate/cis‐diol molar ratios. The aldehyde groups on PAGEO5MA homopolymer were reacted in turn with three amino acids to demonstrate synthetic utility. A water‐soluble aldehyde monomer (AGEO5MA) was prepared by oxidation of GEO5MA at 22 °C. RAFT aqueous polymerization yielded PAGEO5MA homopolymer, which was oxidized using sub‐stoichiometric periodate/cis‐diol molar ratios to yield hydrophilic statistical copolymers with cis‐diol and aldehyde groups. Three PGEO5MA‐based diblock copolymers were converted into aldehyde‐functional copolymers, which were derivatized with amino acids.
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