TITLE

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

AUTHOR(S)
Rahman, M. Mizanur; Takafuji, Makoto; Ihara, Hirotaka
PUB. DATE
November 2008
SOURCE
Analytical & Bioanalytical Chemistry;Nov2008, Vol. 392 Issue 6, p1197
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
ABSTRACT
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.
ACCESSION #
34940167

 

Related Articles

  • Ring-opening polymerization of γ-glycidoxypropyltrimethoxysilane catalyzed by multi-metal cyanide catalyst. Wang, Jingxia; Fan, Xiaodong; Tian, Wei; Wang, Yanli; Li, Juanli // Journal of Polymer Research;Nov2011, Vol. 18 Issue 6, p2133 

    Ring-opening polymerizations of γ-glycidoxypropyltrimethoxysilane (GPTMS) were carried out by using multi-metal cyanide (MMC) catalyst and the synthesized homopolymer was a comb-shaped polymer with regular structure. The structure of the polymer obtained (P-GPTMS) was characterized by FTIR,...

  • The Microbial Transformation of Phenanthrene and Anthracene. Baboshin, M. A.; Baskunov, B. P.; Finkelstein, Z. I.; Golovlev, E. L.; Golovleva, L. A. // Microbiology (00262617);May2005, Vol. 74 Issue 3, p303 

    The transformation of phenanthrene and anthracene by Rhodococcus rhodnii 135, Pseudomonas fluorescens 26K, and Arthrobacter sp. K3 is studied. Twenty-one intermediates of phenanthrene and anthracene transformation are identified by HPLC, mass spectrometry, and NMR spectroscopy. P. fluorescens...

  • A Novel Thiophene-Fused Polycyclic Aromatic with a Tetracene Core: Synthesis, Characterization, Optical and Electrochemical Properties. Zong-Fan Duan; Xian-Qiang Huang; Zhi-Gang Yang; Hoshino, Daiki; Kitanaka, Susumu; Gao-Yang Zhao; Nishioka, Yasushiro // Molecules;Jun2011, Vol. 16 Issue 6, p4467 

    FeCl3-mediated oxidative cyclization was successfully used to construct an extended thiophene-pendant pyrene skeleton and synthesize a novel thiophene-fused polycyclic aromatic (THTP-C) with a tetracene core. The identity of the compound was confirmed by 1H-NMR, 13C-NMR, MS, and elemental...

  • Thermolysis of 3-Azido-N-Phenylthieno-[2,3-b]pyridine-2-Carboxamides. Kanishcheva, E. A.; Vasilin, V. K.; Stroganova, T. A.; Krapivin, G. D. // Chemistry of Heterocyclic Compounds;Dec2013, Vol. 49 Issue 9, p1387 

    The article focuses on the study which examines the synthesis of 1,4-diazepines condensed with a thienopyridine fragment using the preparation of polycyclic 1,4-diazepine derivatives. The study used the N-phenyl-substituted tertiary 3-aminothieno(2,3-b)pyridine-2-carboxamides 1a-c as its...

  • Relation Between Reactivities of Vinyl Monomers and Their NMR Spectra. Hatada, Koichi; Kitayama, Tatsuki; Nishiura, Takafumi; Shibuya, Wataru // Current Organic Chemistry;Feb2002, Vol. 6 Issue 2, p121 

    The ¹sup3;C-NMR chemical shifts of β-carbon (δCβ ) in the vinyl group of various monomers, which depend on the π-electron density on the carbon, were correlated with their reactivity parameters in polymerization reactions. The relations were studied between the δCβ and the...

  • Improvement of catalytic activity and comonomer response in ethylene/norbornene copolymerization initiated with ansa-metallocene. Lee, Dong-ho; Choi, Yi Yeong; Lee, Jo Hoon; Park, Yoon Seok; Woo, Sang Sun // e-Polymers;Nov2001, p1 

    Cites findings of a study conducted to assess catalytic activity and comonomer response in ethylene/norbornene copolymerization initiated with ansa-metallocene. Observation in the catalyst activity with the addition of a small amount of third monomer; Findings of nuclear magnetic resonance...

  • Enzymatic polymerization of m-substituted phenols in the presence of 2,6-di-O-methyl-&Bbeta;-cyclodextrin in water. Tonami, Hiroyuki; Uyama, Hiroshi; Kobayashi, Shiro; Reihmann, Matthias; Ritter, Helmut // e-Polymers;Feb2002, p1 

    Presents a study that deals with enzymatic polymerization of m-substituted phenols in the presence of 2,6-di-O-methyl-&Bbeta;-cyclodextrin in water. Discussion on Horseradish peroxidase polymerizations; M-substituted phenols used in the study; Use of nuclear magnetic resonance spectroscopy to...

  • Correlation between bowl-inversion energy and bowl depth in substituted sumanenes. Shrestha, Binod Babu; Karanjit, Sangita; Higashibayashi, Shuhei; Sakurai, Hidehiro // Pure & Applied Chemistry;May2014, Vol. 86 Issue 5, p747 

    The correlation between the bowl-inversion energy and the bowl depth for sumanenes monosubstituted with an iodo, formyl, or nitro group was investigated experimentally and by theoretical calculations. The bowl-inversion energies of the substituted sumanenes were determined experimentally by...

  • Use of Long-Range C-H Heteronuclear Multiple Bond Connectivity in the Assignment of the 13 C NMR Spectra of Complex Organic Molecules. Araya-Maturana, Ramiro; Delgado-Castro, Tomas; Cardona, Wilson; Weiss-Lopez, Boris E. // Current Organic Chemistry;Mar2001, Vol. 5 Issue 3, p253 

    The structural elucidation of complex organic molecules relies heavily on the application of proton detected heteronuclear NMR. Among these techniques, the HMBC NMR experiment is probably the most useful 2D NMR method The HMBC (C-H) experiment allows the assignment of structural fragments...

Share

Read the Article

Courtesy of VIRGINIA BEACH PUBLIC LIBRARY AND SYSTEM

Sorry, but this item is not currently available from your library.

Try another library?
Sign out of this library

Other Topics