Synthesis and enantioseparation of proline-derived helical polyacetylenes as chiral stationary phases for HPLC

Literature Information

Publication Date 2020-04-09
DOI 10.1039/D0PY00205D
Impact Factor 5.582
Authors

Ge Shi, Xiao Dai, Yue Zhou, Jie Zhang, Jun Shen, Xinhua Wan


View Original

Abstract

Optically active helical poly(phenylacetylene)s (PPAs) have demonstrated themselves as excellent candidates for chiral stationary phases (CSPs) of high-performance liquid chromatography, but the potential of aliphatically substituted polyacetylenes remains unrevealed. Herein, four proline-derived acetylene monomers, (S)-N-aromatic carbamoyl-2-ethynyl pyrrolidine, are prepared and converted to the corresponding conjugated polymers. The asymmetric induction from the directly attached chiral pyrrolidine rings makes the polyene backbones take stable helical conformations with an excess screw sense, which in turn orient the N-aromatic carbamoyl groups to twist along the polymer backbones. The thus formed coaxial double helices endow these polymers with enantioseparation performance comparable to the currently available PPA-based CSPs in terms of the scope of the racemates that can be stereoselectively recognized. Experimental and molecular docking results suggest that the strength of the hydrogen bond and π–π interactions between enantiomers and CSPs are critical for chiral discrimination in addition to the helical polymer scaffold. This work provides an alternative route to develop CSPs with a good enantioseparation ability from biomass other than polysaccharides.

Related Literature

A mimotope attached to an ITIM–SHP-1 interaction inhibitory peptide boosts immune response and efficacy

Koushik Roy, Syamal Roy, Siddhartha Roy

2021-05-19 Research Article

DOI: 10.1039/D1MD00099C

Discovery, synthesis and biological characterization of a series of N-(1-(1,1-dioxidotetrahydrothiophen-3-yl)-3-methyl-1H-pyrazol-5-yl)acetamide ethers as novel GIRK1/2 potassium channel activators

Swagat Sharma, Lauren Lesiak, Christopher D. Aretz, Yu Du, Sushil Kumar, Nagsen Gautam, Yazen Alnouti, Nikilesh V. Dhuria, Yashpal S. Chhonker, C. David Weaver, Corey R. Hopkins

2021-06-21 Research Article

DOI: 10.1039/D1MD00129A

Pyridazinone derivatives as potential anti-inflammatory agents: synthesis and biological evaluation as PDE4 inhibitors

Ingrid Allart-Simon, Aurélie Moniot, Nicolo Bisi, Miguel Ponce-Vargas, Sandra Audonnet, Marie Laronze-Cochard, Janos Sapi, Eric Hénon, Frédéric Velard, Stéphane Gérard

2021-03-01 Research Article

DOI: 10.1039/D0MD00423E

Irreversible inhibition of BoNT/A protease: proximity-driven reactivity contingent upon a bifunctional approach

Lewis D. Turner, Lucy Lin, Sabine Pellett, Takashi Sugane, Eric A. Johnson, Kim D. Janda

2021-05-19 Research Article

DOI: 10.1039/D1MD00089F

Medicines for millions of patients

David C. Rees

2021-11-11 Opinion

DOI: 10.1039/D1MD00279A

Synthesis and evaluation of pyridine-derived bedaquiline analogues containing modifications at the A-ring subunit

Lisa Barbaro, Gayathri Nagalingam, James A. Triccas, Jonathan B. Baell, Daniel L. Priebbenow

2021-05-07 Research Article

DOI: 10.1039/D1MD00063B

The medicinal chemistry of mitochondrial dysfunction: a critical overview of efforts to modulate mitochondrial health

Maximillian Taro William Lee, William Mahy, Mark David Rackham

2021-06-04 Review Article

DOI: 10.1039/D1MD00113B

Drugging the undruggable: a computational chemist's view of KRASG12C

Michael S. Bodnarchuk, Doyle J. Cassar, Jason G. Kettle, Graeme Robb, Richard A. Ward

2021-03-29 Research Article

DOI: 10.1039/D1MD00055A

Mycobacterial drug discovery

Katherine A. Abrahams, Gurdyal S. Besra

2020-11-06 Review Article

DOI: 10.1039/D0MD00261E

You might also like

Compound Q&A

What are the main uses of (3alpha,5alpha)-3-Hydroxypregnane-11,20-dione (CAS: 23930-19-0)?

(3alpha,5alpha)-3-Hydroxypregnane-11,20-dione is primarily used in the pharmaceu...

23930-19-0(3alpha,5alpha)-3-Hy...
Compound Q&A

What is the market or research trend for 4-Amino-6-chloro-2-pyridinecarboxylic acid (CAS: 546141-56-4)?

The market for 4-Amino-6-chloro-2-pyridinecarboxylic acid (CAS: 546141-56-4) is ...

546141-56-44-Amino-6-chloro-2-p...
Compound Q&A

Are there alternatives to (2-Benzoylethyl)trimethylammonium chloride (CAS: 24472-88-6) in synthesis?

Alternatives to (2-Benzoylethyl)trimethylammonium chloride (CAS: 24472-88-6) in ...

24472-88-6(2-Benzoylethyl)trim...
Compound Q&A

Is N-[4-Nitro-3-(trifluoromethyl)phenyl]acetamide (CAS: 393-12-4) safe?

N-[4-Nitro-3-(trifluoromethyl)phenyl]acetamide (CAS: 393-12-4) is generally safe...

393-12-4N-[4-Nitro-3-(triflu...
Compound Q&A

Are there alternatives to N,N'-Bis(3-aminopropyl)-1,3-propanediamine (CAS: 4605-14-5) in synthesis?

There are alternatives to N,N'-Bis(3-aminopropyl)-1,3-propanediamine (CAS: 4605-...

4605-14-5N,N'-Bis(3-aminoprop...
Compound Q&A

What precautions should be taken when handling Aluminium trihexadecanoate (CAS: 555-35-1)?

When handling Aluminium trihexadecanoate, it is important to use appropriate per...

555-35-1Aluminium trihexadec...
Compound Q&A

What is (1,1-Dioxido-3-oxo-1,2-benzothiazol-2(3H)-yl)acetic acid (CAS: 52188-11-1)?

(1,1-Dioxido-3-oxo-1,2-benzothiazol-2(3H)-yl)acetic acid is a chemical compound ...

52188-11-1(1,1-Dioxido-3-oxo-1...
Compound Q&A

Are there alternatives to 5,5-dimethyloxolan-2-one (CAS: 3123-97-5) in synthesis?

Several alternatives to 5,5-dimethyloxolan-2-one (CAS: 3123-97-5) can be used in...

3123-97-55,5-dimethyloxolan-2...

Source Journal

Polymer Chemistry

Polymer Chemistry
CiteScore: 8.6
Self-citation Rate: 7.3%
Articles per Year: 457

Polymer Chemistry welcomes submissions in all areas of polymer science that have a strong focus on macromolecular chemistry. Manuscripts may cover a broad range of fields, yet no direct application focus is required.

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.