Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Chemical Synthesis of Oligodeoxyribonucleotide ; Improvement of Deoxyribonucleoside Phosphorylation and Dideoxyribonucleotide Synthesis

Oligodeoxyribonucleotide의 화학적 합성 ; Deoxyribonucleoside의 인산화와 이량체 합성 방법의 개선

  • 이상직 (영남대학교 이과대학 화학과) ;
  • 송병수 (영남대학교 이과대학 화학과) ;
  • 김종대 (영남대학교 이과대학 화학과)
  • Published : 1987.02.20
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Abstract

The study was done with a focus on making the optimum condition on phosphorylation of deoxyribonucleoside with o-chlorophenylphosphoroditriazole as a phosphorylating agent. The result showed that the addition of 5 volume % pyridine to the dioxane solution accelerated the rate of reaction to a great extent and turned out to nearly quantitative yields on phosphorylation. On the basis of this improvement of optimum reaction conditions, a more efficient method to synthesize all-protected dideoxyribonucleotide from N, 5-O-blocked deoxyribonucleoside was developed. The dodecamer with a Hind Ⅲ recognition site was readily synthesized from five different dimers which were prepared through the newly improved method.

Base의 아미노기와 5'-산소가 아실 및 dimethoxytrityl기로 각각 보호된 deoxyribonucleosidedml 3'-산소를 인산화시약인 o-chlorophenylphosphoroditriazole과 반응시켜 인산화중간체를 합성함에 있어서 수득률을 증가시킬 수 있는 반응조건을 조사하였다. 이 과정에서 주로 이용하고 있는 디옥산단일용매 보다 디옥산에 소량(5%)의 피리딘을 포함시키면 반응속도가 크게 증가하였으며, 단일용매 사용에서의 단점인 부반응도 일어나지 않았다. 인산화방법이 개선되므로 인산화중간체의 합성을 포함한 몇 단계의 반응을 쉽게 수행하여 모두 보호된 이량체를 합성하는 방법을 개발했다. 이렇게 개선된 방법으로 합성한 5종의 이량체들로부터 Hind Ⅲ인식자리를 지닌 십이량체를 합성하였다.

Keywords

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