Application of pH-responsive methylpropargyl leucine polymer in enantioselective crystallization

Jie Zhang; Ningyu Chen; Yuheng Cui; Liqun Zhang; Dongmei Yue

doi:10.1016/j.reactfunctpolym.2016.02.006

Application of pH-responsive methylpropargyl leucine polymer in enantioselective crystallization

Jie Zhang
, Ningyu Chen
, Yuheng Cui
, Liqun Zhang
, Dongmei Yue

Beijing University of Chemical Technology
Key Laboratory of Beijing City on Preparation and Processing of Novel Polymer Materials

科研成果: 期刊稿件 › 文章 › 同行评审

2 引用（Scopus）

摘要

In this study, novel 1-methylpropargyl alcohol derivatives containing leucine side groups on their side chains were successfully synthesized and polymerized using (nbd)Rh⁺[η⁶-C₆H₅B^-(C₆H₅)₃] as catalyst. Circular dichroism (CD) and ultraviolet-visible (UV-Vis) spectra revealed that the polymers took predominantly one-handed helical structures that were stable under heat. Deprotection of the t-butyloxycarboryl (Boc) groups in the homopolymers under acidic conditions produced polymers with primary amine moieties on the side chains. The polymers were soluble in aqueous medium, and turbidity test revealed that they were pH-responsive. Amino acid-based polymers were further used in the enantionselective crystallization of alanine enantiomers and l-alanine was preferably induced to crystallize with the l-leucine-based polymer.

源语言	英语
页（从-至）	63-69
页数	7
期刊	Reactive and Functional Polymers
卷	101
DOI	https://doi.org/10.1016/j.reactfunctpolym.2016.02.006
出版状态	已出版 - 4月 2016
已对外发布	是

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10.1016/j.reactfunctpolym.2016.02.006

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@article{02b20692d47740fbbed41be2c8efade6,

title = "Application of pH-responsive methylpropargyl leucine polymer in enantioselective crystallization",

abstract = "In this study, novel 1-methylpropargyl alcohol derivatives containing leucine side groups on their side chains were successfully synthesized and polymerized using (nbd)Rh+[η6-C6H5B-(C6H5)3] as catalyst. Circular dichroism (CD) and ultraviolet-visible (UV-Vis) spectra revealed that the polymers took predominantly one-handed helical structures that were stable under heat. Deprotection of the t-butyloxycarboryl (Boc) groups in the homopolymers under acidic conditions produced polymers with primary amine moieties on the side chains. The polymers were soluble in aqueous medium, and turbidity test revealed that they were pH-responsive. Amino acid-based polymers were further used in the enantionselective crystallization of alanine enantiomers and l-alanine was preferably induced to crystallize with the l-leucine-based polymer.",

keywords = "Enantionselective crystallization, Helical polymer, Leucine, Polyacetylene, pH-responsive",

author = "Jie Zhang and Ningyu Chen and Yuheng Cui and Liqun Zhang and Dongmei Yue",

year = "2016",

month = apr,

doi = "10.1016/j.reactfunctpolym.2016.02.006",

language = "英语",

volume = "101",

pages = "63--69",

journal = "Reactive and Functional Polymers",

issn = "1381-5148",

publisher = "Elsevier B.V.",

}

TY - JOUR

T1 - Application of pH-responsive methylpropargyl leucine polymer in enantioselective crystallization

AU - Zhang, Jie

AU - Chen, Ningyu

AU - Cui, Yuheng

AU - Zhang, Liqun

AU - Yue, Dongmei

PY - 2016/4

Y1 - 2016/4

N2 - In this study, novel 1-methylpropargyl alcohol derivatives containing leucine side groups on their side chains were successfully synthesized and polymerized using (nbd)Rh+[η6-C6H5B-(C6H5)3] as catalyst. Circular dichroism (CD) and ultraviolet-visible (UV-Vis) spectra revealed that the polymers took predominantly one-handed helical structures that were stable under heat. Deprotection of the t-butyloxycarboryl (Boc) groups in the homopolymers under acidic conditions produced polymers with primary amine moieties on the side chains. The polymers were soluble in aqueous medium, and turbidity test revealed that they were pH-responsive. Amino acid-based polymers were further used in the enantionselective crystallization of alanine enantiomers and l-alanine was preferably induced to crystallize with the l-leucine-based polymer.

AB - In this study, novel 1-methylpropargyl alcohol derivatives containing leucine side groups on their side chains were successfully synthesized and polymerized using (nbd)Rh+[η6-C6H5B-(C6H5)3] as catalyst. Circular dichroism (CD) and ultraviolet-visible (UV-Vis) spectra revealed that the polymers took predominantly one-handed helical structures that were stable under heat. Deprotection of the t-butyloxycarboryl (Boc) groups in the homopolymers under acidic conditions produced polymers with primary amine moieties on the side chains. The polymers were soluble in aqueous medium, and turbidity test revealed that they were pH-responsive. Amino acid-based polymers were further used in the enantionselective crystallization of alanine enantiomers and l-alanine was preferably induced to crystallize with the l-leucine-based polymer.

KW - Enantionselective crystallization

KW - Helical polymer

KW - Leucine

KW - Polyacetylene

KW - pH-responsive

UR - https://www.scopus.com/pages/publications/84958980185

U2 - 10.1016/j.reactfunctpolym.2016.02.006

DO - 10.1016/j.reactfunctpolym.2016.02.006

M3 - 文章

AN - SCOPUS:84958980185

SN - 1381-5148

VL - 101

SP - 63

EP - 69

JO - Reactive and Functional Polymers

JF - Reactive and Functional Polymers

ER -

Application of pH-responsive methylpropargyl leucine polymer in enantioselective crystallization

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