Synthesis and assessment of molecular recognizability by RP-HPLC of an N-alkyl-beta-Ala-L: -Phe-derived organic phase with self-assembling ability.
An N-alky-beta-Ala-L: -Phe derivative, N'-octadecyl-N ( alpha )-[(N-acryloyl)-beta-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 ( alpha )-(acryloyl)-L: -phenylalanineamide (2) without beta -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 (13)C and (29)Si CP-MAS NMR spectroscopic measurements.
Rahman
M Mizanur
MM
Department of Applied Chemistry and Biochemistry, Faculty of Engineering, Kumamoto University, 2-39-1 Kurokami, Kumamoto, 860-8555, Japan.
Takafuji
Makoto
M
Ihara
Hirotaka
H