Lipase-catalyzed synthesis of chiral poly(ester amide)s with an alternating sequence of hydroxy acid and l/d-aspartate units†,Polymer Chemistry

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Lipase-catalyzed synthesis of chiral poly(ester amide)s with an alternating sequence of hydroxy acid and l/d-aspartate units†
Polymer Chemistry ( IF 4.1 ) Pub Date : 2018-02-28 00:00:00 , DOI: 10.1039/c7py01936j
Yiru Liang _{1,

2,

3,

4} , Yu Zhang _{1,

2,

3,

4} , Yujing Hu _{1,

2,

3,

4} , Bo Xia _{4,

5,

6,

7} , Xianfu Lin _{1,

2,

3,

4} , Qi Wu _{1,

2,

3,

4}

Affiliation

Most of reported synthesis approaches for poly(ester amide)s suffer from the difficulty in controlling the sequence of amino acid and ester units, and also some environmental disadvantages. Herein, we developed a facile approach for the lipase-catalyzed synthesis of chiral L-/D-Asp-based poly(ester amide)s with alternating aspartate and hydroxyhexanoic acid (HA) units. In the Novozym 435-catalyzed polycondensation starting from four monomers, namely N-(6-hydroxyhexanoyl) aspartate diesters with an L- or D-aspartate configuration, and methyl or benzyl ester groups at the α or β-carbonyl positions of Asp, we successfully obtained the corresponding alternating poly(HA-alt-L/D-β-aspartate)s with α-benzyl or α-methyl ester groups. The L-aspartate diester monomer was preferred to the D-aspartate diester monomer in the Novozym 435-catalyzed polycondensation, and it also showed high regioselectivity, mainly forming the β-linkage of the aspartate unit. Among the four poly(ester amide)s, poly(HA-alt-L-α-benzyl-β-aspartate) has the highest molar mass of up to 13 000 Da and 98% β-linkage. The thermal properties and the aggregate microstructures of these alternating poly(HA-alt-L/D-aspartate)s were also compared and some interesting differences were observed. Our results also showed that these enantiopure poly(HA-alt-L/D-aspartate)s did not form a stereocomplex.

中文翻译：

脂肪酶催化合成具有羟基酸和l / d-天冬氨酸单元交替序列的手性聚（酯酰胺）†

大多数报道的用于聚（酯酰胺）的合成方法都难以控制氨基酸和酯单元的序列，并且还具有一些环境不利因素。在这里，我们开发了一种简便的方法，用于脂肪酶催化的手性L- / D -Asp基聚（酯酰胺）与天冬氨酸和羟基己酸（HA）单元交替出现的合成。在Novozym 435催化的缩聚反应中，从四个单体开始，即具有L-或D-天冬氨酸构型的N-（6-羟基己酰基）天冬氨酸二酯，以及Asp的α或β-羰基位置的甲基或苄基酯基，成功地获得相应的交替的聚（HA- ALT -具有α-苄基或α-甲基酯基的L / D -β-天冬氨酸）。的大号天冬氨酸二酯单体优选将d天冬氨酸二酯单体在诺维信435催化的缩聚，并且它还表现出较高的区域选择性，主要形成天冬氨酸单元的β-联动。在这四种聚（酯酰胺）中，聚（HA - alt - L -α-苄基-β-天冬氨酸）的最高摩尔质量高达13000 Da，β-键合率为98％。这些交替的聚（HA- alt - L / D）的热学性质和聚集的微观结构-天冬氨酸）也进行了比较，观察到一些有趣的差异。我们的结果还表明，这些对映体纯的聚（HA- alt - L / D-天冬氨酸）不会形成立体复合物。

更新日期：2018-02-28

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