• 제목/요약/키워드: Binaphthyl

검색결과 26건 처리시간 0.02초

Preparation of New Binaphthol Derived Chiral Stationary Phases

  • Zhang, Yi Jun;Ryoo, Jae-Jeong
    • Bulletin of the Korean Chemical Society
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    • 제32권8호
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    • pp.2756-2760
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    • 2011
  • To develop more advanced binaphthol derived CSPs, two new 1,1-bi-2-naphthol derived chiral stationary phases (CSPs) (CSP 1 and CSP 2) were prepared by connecting with silica gel at a hydroxy (OH) group of binaphthol. Previously reported two 1,1'-binaphthyl-2,2'-diamine derived CSPs (CSP 3 and CSP 4) were also prepared to compare the role of their functional groups (-OH and -$NH_2$) with CSP 1 and CSP 2. Enantioseparation of randomly selected, 11 chiral compounds on these four CSPs was performed and the results compared to each other. 3,5-Dinitrobenzoyl (3,5-DNB) derivatives of each CSP showed better results than the others and binaphthyldiamine derived CSP showed slightly better than binaphthol derived one.

Facile Synthesis of the Uryl Pendant Binaphthol Aldehyde and Its Selective Fluorescent Recognition of Tryptophan

  • Tang, Lijun;Wei, Gongfan;Nandhakumar, Raju;Guo, Zhilong
    • Bulletin of the Korean Chemical Society
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    • 제32권9호
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    • pp.3367-3371
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    • 2011
  • An easy and convenient synthetic route to (S)-2-hydroxy-2'-(3-phenyluryl-benzyl)-1,1'-binaphthyl-3-carboxaldehyde (1), capable of recognizing tryptophan by fluorescence has been developed. The binol carboxaldehyde 1 exhibited a high selectivity to L-tryptophan over other examined L-${\alpha}$-amino acids such as alanine, phenylalanine, glutamine, arginine, lysine, serine, threonine, aspartat, valine, histidine and cysteine, with a fluorescence "turn-on" signal. In addition, 1 displayed chiral discrimination with good enantioselectivity toward L-tryptophan over D-tryptophan through different fluorescence enhancement factors.

Development and Application of Crown Ether-based HPLC Chiral Stationary Phases

  • Hyun, Myung-Ho
    • Bulletin of the Korean Chemical Society
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    • 제26권8호
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    • pp.1153-1163
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    • 2005
  • Crown ether-based HPLC chiral stationary phases (CSPs) have been successfully utilized in the resolution of various racemic compounds containing a primary amino group. Especially, CSPs based on chiral crown ethers incorporating chiral binaphthyl unit or tartaric acid unit and based on phenolic pseudo chiral crown ethers have shown high chiral recognition efficiency. In this account paper, a review on the development of crown etherbased HPLC CSPs, their structural characteristics and applications to the resolution of racemic compounds including chiral drugs containing a primary or secondary amino group with the variation of the type and the content of mobile phase components and with the variation of the column temperature is presented.

Investigation of Enantiomer Separation Using Chiral Crown Ethers as Chiral Selectors

  • Lee, Wonjae
    • 통합자연과학논문집
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    • 제9권1호
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    • pp.28-34
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    • 2016
  • A number of chiral selectors have been developed and applied for enantiomer separation of a variety of chiral compounds. Among these chiral selectors are chiral crown ethers, a class of synthetic host polyether molecules that bind protonated chiral primary amines with high selectivity and affinity. In this paper, two important chiral crown ethers as chiral selectors of bis-(1,1'-binaphthyl)-22-crown-6 and (18-crown-6)-2,3,11,12-tetracarboxylic acid (18-C-6-TA) are focused. They have been widely used to resolve the enantiomers of chiral compounds containing a primary amino moiety using chiral stationary phases (CSPs) or chiral selectors by high-performance liquid chromatography (HPLC), capillary electrophoresis (CE) and so on in chirotechnology. Also, it was described that the commercially available covalent type HPLC CSPs derived from (+)- and (-)-18-C-6-TA have been developed and successfully applied for the resolution of various primary amino compounds including amino acids.

광학분리를 위한 키랄 크라운 에테르를 이용한 키랄공학의 개발과 응용 (The Development and Application of Chirotechnology Using Chiral Crown Ethers for Enantiomer Separation)

  • 백만정;윤원남;이원재
    • KSBB Journal
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    • 제27권4호
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    • pp.199-206
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    • 2012
  • Chiral crown ethers are synthetic macrocyclic polyethers that bind protonated chiral primary amines with high selectivity and affinity. They have been widely used to separate or distinguish the enantiomers of chiral compounds containing a primary amino moiety by high-performance liquid chromatography, capillary electrophoresis, and NMR spectroscopy. In this paper, two important chiral crown ethers including chiral binaphthyl unit and (18-crown-6)-2,3,11,12-tetracarboxylic acid as chiral selectors are focused. And several chiral resolution techniques and their applications in chirotechnology using these chiral crown ethers with related chiral recognition mechanism studies are reviewed. Especially, it was shown that the commercially available HPLC columns based on (18-crown-6)-2,3,11,12-tetracarboxylic acid have been developed and successfully applied for the resolution of various primary amino compounds including amino acids.

Novel Silver(I) Ion Selective PVC Membrane Electrode Based on the Schiff Base (N2E,N2'E)-N2,N2'-Bis(Thiophen-2-ylmethylene)-1,1'-Binaphthyl-2,2'-Diamine

  • Jeong, Eunseon;Ahmed, Mohammad Shamsuddin;Jeong, Hae-Sang;Lee, Eun-Hee;Jeon, Seung-Won
    • Bulletin of the Korean Chemical Society
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    • 제32권3호
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    • pp.800-804
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    • 2011
  • A potentiometric sensor based on the Schiff base $(N^2E,N^{2'}E)-N^2,N^{2'}$-bis(thiophen-2-ylmethylene)-1,1'-binaphthl-2,2'-diamine has been synthesized and explored as an ionophore PVC-based membrane sensor selective for the silver ($Ag^+$) ion. Potentiometric investigations indicate a high affinity of this receptor for the silver ion. Seven membranes have been fabricated with different compositions, with the best performance shown by the membrane with an ionophore composition (w/w) of: 1.0 mg, PVC: 33.0 mg, DOA: 66.0 mg in 1.0 mL THF. The sensor worked well within a wide concentration range of $1.0{\times}10^{-2}$ to $1.0{\times}10^{-7}$ M, at pH 5, at room temperature (slope 57.4 mV/dec.), and with a rapid response time of 9 s; the sensor also showed good selectivity towards the silver ion over a huge number of interfering cations, with the highest selectivity coefficient for $Hg^{2+}$ at -3.7. Thus far, the best lower detection limit was $4.0{\times}10^{-8}$ M.