• 제목/요약/키워드: N-FMOC$\alpha$-amino acids

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Liquid Chromatographic Reaolution of N-Protected α -Amino Acids as Their Anilide and 3,5-Dimethylanilide Derivatives on Chiral Syationary Phases Derived fron (S)-Leucine

  • Hyun, Myung-Ho;Cho, Yoon-Jae;Baik, In-Kyu
    • Bulletin of the Korean Chemical Society
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    • 제23권9호
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    • pp.1291-1294
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    • 2002

  • Various racemic N-protected ${\alpha}-amino$ acids such as N-t-BOC-(tert-butoxycarbonyl), N-CBZ-(benzyloxycarbonyl) and N-FMOC-(9-fluorenylmethyloxycarbonyl) ${\alpha}-amino$ acids were resolved as their anilide and 3,5-dimethylanilde derivatives on an HPLC chira l stationary phase (CSP) developed by modifying a commercial (S)-leucine CSP. The chromatographic resolution results were compared to those on the commercial (S)-leucine CSP. The resolutions were greater on the modified CSP than those on the commercial CSP with only one exception, the resolution of N-t-BOC-phenylglycine anilide. In addition, the chromatographic resolution behaviors were quite consistent except for the resolution of N-protected phenylglycine derivatives, the (S)-enantiomers being retained longer. Based on the chromatographic resolution behaviors and with the aid of CPK molecular model studies, we proposed a chiral recognition mechanism for the resolution of N-protected ${\alpha}-amino$ acid derivatives. However, for the resolution of N-protected phenylglycine derivatives, a second chiral recognition mechanism, which competes in the opposite sense with the first chiral recognition mechanism, was proposed. The two competing chiral recognition mechanisms were successfully used in the rationalization of the chromatographic behaviors for the resolution of N-protected phenylglycine derivatives.

  • https://doi.org/10.5012/bkcs.2002.23.9.1291 인용 PDF KSCI

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

  • 하병조;이윤식;박수남
    • 대한화장품학회지
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    • 제30권3호
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    • pp.399-404
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    • 2004

  • 새로운 Gly-His-Lys (약자로 GHK)가 결합된 키토산을 $N^{\alpha}-Fmoc$ 아미노산과 BOP 커플링 시약을 사용한 고상법에 의해 제조하였다. 이를 위해 키토산 마이크로 비드를 W/O 에멀젼 상분리법으로 평균 입자크기 70 마이크로미터로 얻었다. GHK 펩타이드는 순차적으로 고상법에 의해 키토산 마이크로비드 위에 커플링 하였다. 아미노산 분석을 실시한 결과 Gly, His, kys의 비율이 1.02:1.13:0.96의 비율로 나타나 이론치와 거의 일치함을 확인할 수 있었다. GHK 펩타이드가 결합된 마이크로비드의 세포증식 효과는 MTT 분석으로 측정하였다. 측정결과 GHK 펩타이드가 결합된 키토산 마이크로비드는 대조군인 펩타이드가 결합되지 않은 키토산 마이크로비드 자체에 비해 높은 세포증식 효과를 보였다.

  • PDF KSCI