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2-氧代-2H-苯并[h]苯并吡喃作为一种新的光敏感保护基团用于神经递质氨基酸。

2-Oxo-2H-benzo[h]benzopyran as a new light sensitive protecting group for neurotransmitter amino acids.

机构信息

Centro de Química, Universidade do Minho, Campus de Gualtar, 4710-057, Braga, Portugal.

出版信息

Amino Acids. 2010 Jun;39(1):121-33. doi: 10.1007/s00726-009-0383-z. Epub 2009 Nov 12.

DOI:10.1007/s00726-009-0383-z
PMID:19908122
Abstract

Aiming at the development of new benzopyran-based photocleavable protecting groups, novel chloromethylated and hydroxymethylated 2-oxo-2H-benzo[h]benzopyran derivatives bearing a methoxy substituent were designed and used in the synthesis of a series of fluorescent bioconjugates, by linking through an ester or urethane bond to several model neurotransmitter amino acids (glycine, alanine, beta-alanine and gamma-aminobutyric acid, GABA). The resulting fluorescent bioconjugates with emission in the visible range and high fluorescent quantum yields, were subjected to photocleavage reaction in methanol/HEPES buffer (80:20) solution at different wavelengths of irradiation (250, 300, 350 and 419 nm) and photocleavage kinetic data were obtained.

摘要

针对新型苯并吡喃类光解保护基团的发展,设计了新型氯甲基和羟甲基化的 2-氧代-2H-苯并[h]苯并吡喃衍生物,带有甲氧基取代基,并用于通过酯或氨酯键与几种模型神经递质氨基酸(甘氨酸、丙氨酸、β-丙氨酸和γ-氨基丁酸(GABA))合成一系列荧光生物缀合物。得到的在可见范围内发射且具有高荧光量子产率的荧光生物缀合物,在甲醇/HEPES 缓冲液(80:20)溶液中在不同的辐照波长(250、300、350 和 419nm)下进行光解反应,并获得光解动力学数据。

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