Influence of Helical Structure on Chiral Recognition of Poly(phenylacetylene)s Bearing Phenylcarbamate Residues of L‐Phenylglycinol and Amide Linage as Pendants. Issue 8 (14th May 2015)

• Record Type: Journal Article
• Authors: Zhang, Chunhong; Ma, Rui; Wang, Hailun; Sakai, Ryosuke; Satoh, Toshifumi; Kakuchi, Toyoji; Liu, Lijia; Okamoto, Yoshio
• Is Part Of: Chirality. Volume 27:Issue 8(2015)
• Page Start: 500
• Page End: 506
• Publication Date: 2015-05-14
• Subjects: Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.22453
• Languages: English
• ISSNs: 0899-0042

Abstract

<abstract abstract-type="main"> <title>Abstract</title> <p>Four poly(phenylacetylene)s (<bold>PPA-1</bold>, <bold>PPA-2</bold>, <bold>PPA-3</bold>, <bold>PPA-4</bold>) bearing phenylcarbamate residues of <sc>L</sc>‐phenylglycinol and amide linkage as pendants were prepared to be used as chiral stationary phases (CSPs) for high‐performance <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">liquid chromatography</named-content> (HPLC), and the influences of coating solvents, dimethylformamide (DMF) and tetrahydrofuran (THF), which were used for coating the polymers on silica gel, on the helical structure of the polymers and their <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">chiral recognition</named-content> abilities were investigated. The structure analysis of <bold>PPA-1</bold>, <bold>PPA-2</bold>, <bold>PPA-3</bold>, <bold>PPA-4</bold> by <sup>1</sup>H <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">nuclear magnetic resonance</named-content> (NMR), size exclusion chromatography (SEC), optical rotation, and circular dichroism (CD) spectra indicated that the polymers possess the cis‐transoidal structure with dynamic helical conformation. The polymers in THF seem to have shorter conjugated helical main chains along with a tighter twist conformation than those in DMF. The <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">chiral recognition</named-content> abilities of <bold>PPA-1</bold>, <bold>PPA-2</bold>, <bold>PPA-3</bold>, <bold>PPA-4</bold> with the different helical structures induced by the coating solvents were evaluated as the CSPs in HPLC. The helical structures of <bold>PPA-1</bold>, <bold>PPA-2</bold>, <bold>PPA-3</bold>, <bold>PPA-4</bold> induced with THF are preferable for <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">chiral recognition</named-content> for some racemates compared to those induced with DMF, and higher <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">chiral recognition</named-content> abilities of <bold>PPA-1</bold>, <bold>PPA-2</bold>, <bold>PPA-3</bold>, <bold>PPA-4</bold> were achieved using THF. <italic>Chirality 27:500–506, 2015</italic>. © 2015 Wiley Periodicals, Inc.</p> </abstract>