Synthesis and assessment of molecular recognizability by RP-HPLC of an N-alkyl- β-Ala- L-Phe-derived organic phase with self-assembling ability

Rahman, M. Mizanur; Takafuji, Makoto; Ihara, Hirotaka
November 2008
Analytical & Bioanalytical Chemistry;Nov2008, Vol. 392 Issue 6, p1197
Academic Journal
An N-alky- β-Ala- L-Phe derivative, N'-octadecyl- N α -[( N-acryloyl)- β-alanyl]- L-phenylalanineamide ( 1), with a polymerizable head group has been synthesized and telomerized with the silane coupling agent 3-mercaptopropyltrimethoxysilane (MPS). SEM and DSC observations indicated that both 1 and its telomer ( T-1) could self-assemble into fibrillar forms with highly ordered structures in organic media such as benzene through complementary hydrogen bonding between the amide moieties. T-1 was grafted onto porous silica gels through the terminal trimethoxysilyl group and then packed into a stainless steel column. RP-HPLC results for polycyclic aromatic hydrocarbons (PAHs) demonstrated that significantly higher molecular shape recognition could be achieved by silica-supported T-1 (Sil- T-1). In this paper, the mechanism of the selectivity enhancement in HPLC by Sil- T-1 is discussed on the basis of comparing with the corresponding L-Phe derivative N'-octadecyl- N α -(acryloyl)- L-phenylalanineamide ( 2) without β -Ala and the stationary phase (Sil- T-2) obtained from it. The HPLC column materials Sil- T-1 and Sil- T-2 were characterized by DSC, TGA, DRIFT-IR, and 13C and 29Si CP-MAS NMR spectroscopic measurements.


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