Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Photochemical Synthesis of Aspartylphenylalanyl Methyl Ester

광 알킬화 반응에 의한 Aspartylphenylalanyl Methyl Ester의 합성

  • Sang Chul Shim (Department of Chemical Science, Korea Advanced Institute of Science) ;
  • Kyu Ho Chae (Department of Chemical Science, Korea Advanced Institute of Science)
  • 심상철 (한국과학기술원 화학 및 화학공학과) ;
  • 채규호 (한국과학기술원 화학 및 화학공학과)
  • Published : 1975.10.30
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Abstract

Glycine residue in N-X-glycylphenylalanine methyl ester(X = trifluoroacetyl or acetyl) was converted into aspartic acid derivative by a photoalkylation reaction. The reaction was induced with 350 nm lamp using a combination of diacetyl/di-t-butyl peroxide (DBP) as the photoinitiator, and acetic anhydride as the alkylating agent. In the thermal reaction with DBP and acetic anhydride, the same alkylation reaction of the dipeptide was observed. From this thermal alkylation reaction the photoalkylation reaction is also thought to undergo via free radical mechanism.

N-X-glycylphenylalanine methyl ester(X-trifluoroacetyl or acetyl)의 글리신잔기를 광 알킬화 반응에 의해 aspartic acid 의 유도체로 전환하였다. 이 반응은 diacetyl/di-t-butyl peroxide(DBP)를 광 개시제로, acetic anhydride를 알킬화제로 하여 350nm 파장의 램프를 사용하므로써 일어난다. DBP와 acetic anhydride에 의한 열반응의 경우에도 같은 알킬화 반응을 관찰하였다. 이 열알킬화 반응은 자유라디칼 반응을 거쳐 일어나기 때문에 이와 비교하여 광 알킬화 반응도 자유라디칼 메카니즘에 의해 일어난 것으로 추측된다.

Keywords

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