PTERIDINES .85. CHEMICAL SYNTHESIS OF DEOXYSEPIAPTERIN AND 6-ACYLPTERIDINES BY ACYL RADICAL SUBSTITUTION-REACTIONS
PTERIDINES .85. CHEMICAL SYNTHESIS OF DEOXYSEPIAPTERIN AND 6-ACYLPTERIDINES BY ACYL RADICAL SUBSTITUTION-REACTIONS
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DOI：
10.1002/hlca.19880710305
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发表时间：
1988-01-01
影响因子：
1.8
通讯作者：
PFLEIDERER, W
中科院分区：
文献类型：
--
作者：
BAUR, R;SUGIMOTO, T;PFLEIDERER, W
本文报道了果蝇突变体乌贼的两种黄色眼睛色素之一脱氧乌贼蝶呤（2）的新合成方法。该合成方法利用7-（烷硫基）蝶啶衍生物（11，13，15，18，20）的均裂亲核酰化，得到相应的6-酰基衍生物（21-27）。首次在碱性介质中用Raney-Co、Raney-Cu或Cu-Al合金实现了蝶啶系列的脱硫。除了C（7）-S键的断裂之外，检测到C（6）和C（7）=N（8）键处的C=O基团的进一步还原作为副反应，分别产生6-（1-羟基烷基）（34、35、42、43）和6-酰基-7，8-二氢衍生物（2、36、37）。对新合成的化合物进行了元素分析、pK测定、UV和~ 1H-NMR表征。
A new synthesis of deoxysepiapterin (2), one of the two yellow eye pigments of the Drosophila mutant sepia, is described. The synthetic approach makes use of a homolytic nucleophilic acylation of 7-(alkylthio)pteridine derivatives (11, 13, 15, 18, 20) leading to the corresponding 6-acyl derivatives (21-27). Desulfurizations have been achieved for the first time in the pteridine series using Raney-Co, Raney-Cu, or Cu-Al alloy in alkaline medium. Besides cleavage of the C(7)-S bond, further reductions of the C=O group at C(6) and the C(7)=N(8) bond are detected as side reactions leading to 6-(1-hydroxyalkyl) (34, 35, 42, 43) and 6-acyl-7,8-dihydro derivatives (2, 36, 37), respectively. The newly synthesized compounds hve been characterized by elemental analysis, pK determination, UV and 1H-NMR spectra.