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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 39, Number 5
JKCSEZ 39(5)
October 20, 1995 

Theoretical Studies on the Photochemical Reaction of Psoralen Derivatives with Thymine (Ⅳ). Photoadducts of Azapsoralen with Thymine
Ja Hong Kim*, Sung Ho Sohn, Kee Soo Yang, Sung Wan Hong
피부에 대한 광증감 효과를 나타내는 소랄렌의 유도체중 8-azapsoralen 및 4,4',5'-trimethyl-8-azapsoralen과 티민의 전자상태를 반경험적 분자궤도법으로 고찰하였다. 소랄렌 유도체와 티민 사이의 분자착물 형성에서 가능성 있는 배치를 결정하기 위하여 들뜬 상태의 azapsoralen과 바닥상태의 티민의 전하 이동량을 결정하고, 반응 위치인 3,4-탄소와 4',5'-탄소 이중결합과 티민의 5,6-이중결합과의 광부가 생성물의 입체구조는 trans-anti형의 Azaps(3,4)<>Thy(5,6) 결합과 4,4',5'-trimethyl-8-Azaps(3,4)<>Thy(5,6) 결합을 형성한다는 사실을 알았다.

The electronic structure of photoskinsensitizing 8-azapsoralen and 4,4',5'-trimethyl-8-azapsoralen has been investigated by the semiempirical (PM3-CI-UHF, etc) methods. The formation of molecular complexes between ground thymine and excited azapsoralen is discussed in terms of charge transfer interaction. The results indicated that the most probable orientation through C4-cycloaddition of 3,4-double bond of azapsoralen and 5,6-double bond of thymine bases, expecially photoadducts were inferred to be a trans-anti azapsoralen(3,4) < > Thymine(5,6) and trans-anti 4,4',5'-trimethyl-8-azapsoralen (3,4) < > Thymine(5,6).

338 - 343
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