Chemistry of Leucovorin
Chemistry of Leucovorin
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亚叶酸化学
DOI：
10.1021/ja01133a015
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发表时间：
1952
影响因子：
15
通讯作者：
Robert P. Parker
中科院分区：
文献类型：
--
作者：
Donna B. Cosulich;Barbara Roth;James M. Smith;Martin E. Hultquist;Robert P. Parker
通过对亚叶酸素及其相关的甲酰基四氢蝶啶的化学研究，得出亚叶酸素的结构为5-甲酰基- 5,6,7,8 -四氢蝶啶谷氨酸。描述了对柠檬酸白菌8081具有活性的硝酸亚叶酸素。制备了四种亚叶酸素酸转化产物，并对其进行了表征。亚叶酸素(I)的合成是一种翼酰基谷氨酸衍生物，其生物学特性与Sauberlich和Baumann的citrovorum因子（CF） 1相似，这些实验室在早期的通讯中报道过。在对纯结晶合成物质及其转化产物和相关模型化合物进行化学研究的基础上，认为N-（4-[(2-氨基-4-羟基-5-甲酰基- 5,6,7,8 -四氢嘧啶(4,5,b)-吡嗪基-6)-甲基]-氨基苯甲酰）-谷氨酸(I)的结构最可能是leuco-vorin。本文的目的是为这种结构提供新的化学证据。合成亚叶酸素的基本步骤是：还原翼酰谷氨酸（PGA）
From chemical studies on leucovorin and related formyltetrahydropteridines it is concluded that leucovorin has the structure 5-formyl-5, 6, 7, 8-tetrahydropteroylglutamic acid. Leucovorin nitrate, which is active for Leuconostoc citrovorum 8081, is described. Four acid transformation products of leucovorin have been prepared and characterized.The synthesis of leucovorin (I), a pteroylglutamic acid derivative with biological properties similar to the citrovorum factor (CF) 1 of Sauberlich and Baumann, was reported in earlier communications from these laboratories. 2, 3 On the basis of chemical studies on the pure crystalline synthetic substance, its transformation products, and related model compounds, the structure N-(4-[(2-amino-4-hydroxy-5-formyl-5, 6, 7, 8-tetrahydropyrimido (4, 5, b)-pyrazinyl-6)-methyl]-aminobenzoyl)-glutamic acid (I) is considered to be the most probable for leuco-vorin. 4 The purpose of the present paper is to present new chemical evidence for this structure. The essentialsteps in the synthesis3 of leucovorin are: reduction of pteroylglutamic acid (PGA) 6