• Title/Summary/Keyword: FMOC

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Application of FMOC-Cl for the Quantitative Determination of N-linked Oligosaccharides (FMOC 표식에 의한 Sugar Chain의 분석)

  • Kim, Dong-Hyun;Hwangbo, Sik;Chung, Gu-Yong
    • Korean Journal of Food Science and Technology
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    • v.29 no.4
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    • pp.630-634
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    • 1997
  • A fluorescence tagging agent, FMOC-Cl (9-fluorenylmethyl chloroformate) was used for the determination of 1-amino-oligosaccharide intermediates generated from glycoproteins by peptide-N $(N-acetyl-{\beta}-D-glucosaminyl)$ asparagine amidase (N-Glycanase, PNGase F). The derivatives were separated on an Amido 80 column by HPLC using a gradient system with 25 to 51% aqueous acetonitrile and monitored by a fluorometric detector. The detection limit of FMOC-amino-oligosaccharides was $0.05{\sim}1.5$ pmol with fluorometric detection at 278 nm.

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Enantiomer separation using a covalently immobilized chiral column derived from polysaccharide derivative by reversed phase liquid chromatography (역상 크로마토그래피에서 다당유도체로 공유결합된 키랄 컬럼을 이용한 거울상 이성질체의 광학분리)

  • Huang, Hu;Jin, Jing Yu;Baek, Chae-Sun;Lee, Wonjae
    • Analytical Science and Technology
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    • v.22 no.2
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    • pp.148-151
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    • 2009
  • Enantiomer separation of N-fluorenylmethoxycarbonyl (FMOC) $\alpha$-amino acid was performed on covalently immobilized chiral column (Chiralpak IB) based on polysaccharide derivative as a chiral selector by reversed phase liquid chromatography. The effect of the reversed mobile phase on the chromatographic parameters of the enantioselectivities, resolution factors and retention times using covalently immobilized Chiralpak IB was shown. Also the enantiomer separation of N-FMOC $\alpha$-amino acid in the reversed and normal phase was compared and the results obtained in the former mobile phase were generally lower than those in the latter mobile phase.

Identification of Homoserine Lactone Derivatives Using the Methionine Functionalized Solid Phase Synthesis by Gas Chromatography/Mass Spectrometry

  • Moon, Hong-Sik
    • Archives of Pharmacal Research
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    • v.27 no.1
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    • pp.25-30
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    • 2004
  • Combinatorial homoserine lactone mixtures and individual products were obtained from the methionine-functionalized resin in solid-phase synthesis. The four-step process consisting of a coupling step of an N-Fmoc-L-methionine, deprotection of N-Fmoc group, N-coupling with a carboxylic acid, and cleavage reaction through a polymer supported strategy is described. Gas chromatography-mass selective detector (GC-MSD) techniques provide the most powerful methods for identifying both the combinatorial mixtures and individual products.

Screening method for amines by derivatization reaction on TLC (TLC 상 유도체화 반응을 이용한 아민 계 화합물의 Screening 방법)

  • Choi, Sung-Woon;Lee, Hye-In;Sung, Nack-Do
    • Analytical Science and Technology
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    • v.26 no.4
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    • pp.228-234
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    • 2013
  • Methamphetamine is an amine-containing illegal drug and is distributed unlawfully in South Korea. Finding a rapid, convenient and semi-quantitative determination method for methamphetamine is a very important issue in the area of forensic drug testing. As an effort to develop new screening method, the reactions between three organic compounds which are structurally similar to methamphetamine and N-(9-fluorenylmethoxycarbonyloxy) succinimide (FMOC-NHS) were performed on silica gel ($SiO_2$) TLC plates. Three reference compounds were synthesized and used for the identification, comparison and study of the limit of detection (LOD) of the products obtained from a direct reaction on a TLC plate. As a result, FMOC-NHS as a derivatization reagent generated compounds containing highly UV-active functional groups on the TLC plate after reacting with primary- and secondary amines. In the experiment 2D the LOD of amines was in the range of 0.045 and 0.01 mg/mL ($2{\mu}L/spot$), and in 1D the LOD was in the range of 0.002 and 0.007 mg/mL ($2{\mu}L/spot$). The LODs of the compounds tested were dependent on the concentration of the derivatizing reagent.

Simultaneous Enantiomer Separation of α-Amino Acids and Their Esters as Fluorenylmethoxycarbonyl Derivatives under UV and Fluorescence Detection by High Performance Liquid Chromatography (고성능 액체 크로마토그래피에서 아미노산과 이들 에스테르의 플루오레닐메톡시카르보닐 유도체의 자외선과 형광 검출에서의 동시 광학분리)

  • Islam, Md. Fokhrul;Lee, Wonjae
    • KSBB Journal
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    • v.30 no.4
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    • pp.197-201
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    • 2015
  • Liquid chromatographic enantiomer separation of ${\alpha}$-amino acids and their methyl and ethyl esters as fluorenylmethoxycarbonyl (FMOC) derivatives was performed using a recently developed chiral column (Chiralpak IE) based on polysaccharide derivative under simultaneous UV detection and fluorescence detection. The degree of enantiomer separation of ${\alpha}$-amino acid esters as FMOC derivatives is generally higher than that of the corresponding ${\alpha}$-amino acids. Especially, ${\alpha}$-amino acid methyl esters showed the greatest enantioseparation. As this method developed in this study can be applied to determine the chemical and optical purity of ${\alpha}$-amino acids and esters, it is expected to be quite useful for their chiral separation using Chiralpak IE.

Efficient Macrocyclization for Cyclicpeptide Using Solid-Phase Reaction

  • Kim, Joong-Hup;Hong, Il-Khee;Kim, Hyo-Jeong;Jeong, Hyeh-Jean;Choi, Moon-Jeong;Yoon, Chang-No;Jeong, Jin-Hyun
    • Archives of Pharmacal Research
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    • v.25 no.6
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    • pp.801-806
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    • 2002
  • Cyclicpeptides are important targets in peptide synthesis because of their interesting biological properties. Constraining highly flexible linear peptides by cyclization is one of the mostly widely used approaches to define the bioactive conformation of peptides. Cyclic peptides often have increased receptor affinity and metabolic stability over their linear counterparts. We carried out virtual screening experiment via docking in order to understand the interaction between HLE-Human Leukocyte Elastase and ligand peptide and to identify the sequence that can be a target in various ligand peptides. We made cyclic peptides as a target base on Metlle-Phe sequence having affinity for ligand and receptor active site docking. There are three ways to cyclize certain sequences of amino acids such as Met-lie-Phe-Gly-Ile. First is head-to-tail cyclization method, linking between N-terminal and C-terminal. Second method utilizes amino acid side chain such as thiol functional group in Cys, making a thioether bond. The last one includes an application of resin-substituted amino acids in solid phase reaction. Among the three methods, solid phase reaction showed the greatest yield. Macrocyclization of Fmoc-Met-Ile-Phe-Gly-Ile-OBn after cleavage of Fmoc protection in solution phase was carried out to give macrocyclic compound 5 in about 7% yield. In the contrast with solution phase reaction, solid phase reaction for macrocyclization of Met-Ile-Phe-Gly-Ile-Asp-Tentagel in normal concentrated condition gave macrocyclic compound 7 in more than 35% yield.

Determination of Histamine by Reverse-Phase High Performance Liquid Chromatography with Fluorescence Detection (형광검출 역상 액체크로마토그래피에 의한 Histamine의 정량)

  • Ryu, Hee-Chun;Kim, Hyung-Ryong;Kim, Sang-Hyun;Kim, Dae-Ki;Lee, Young-Mi;Kim, Hyung-Min;An, Nyeon-Hyoung;Shin, Tae-Yong
    • Analytical Science and Technology
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    • v.9 no.2
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    • pp.198-202
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    • 1996
  • A rapid and simple method for the determination of histamine by reverse-phase high performance liquid chromatography with fluorescence detection was established. 9-Fluorenylmethyl chloroformate(FMOC) was used as fluorescent derivative reagent. The optimum conditions for the derivatization such as pH, reaction time and the concentration of FMOC were investigated. Linearity of calibration curve was obtained between $0.1{\mu}g/ml$ and $0.5{\mu}g/ml$(r=0.992) and the limit of detection was $0.01{\mu}g/ml$.

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Gly-His-Lys Conjugated Chitosan and its Cell Proliferation Effects (Gly-His-Lys 펩타이드가 결합된 키토산과 그의 세포증식 효과에 관한 연구)

  • Ha Byung-Jo;Lee Yoon-Sik;Park Soo Nam
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.30 no.3 s.47
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    • pp.399-404
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    • 2004
  • Novel GHK-conjugated chitosan was prepared by the solid-phase method using $N^{\alpha}-Fmoc$ amino acids/BOP coupling reagent. For this purpose, the chitosan microbeads which had a mean diameter of 70 um were prepared by the W/O emulsion-phase separation method. The GHK was successfully coupled to the chitosan microbeads by stepwise solid-phase method. The result of amino aid analysis was in good agreement with the theoretical values; $Gly_{1.02}\;of\;His_{1.13}\;Lys_{0.96).$. The cell proliferation effect of the GHK-bound chitosan microbeads was measured by MTT assay. We concluded that GHK-bound chitosan microbeads gave higher cell Proliferation effect than chitosan microbeads.