PREPARATION OF CRYSTALLINE PHOSPHORYLATED DERIVATIVES OF VITAMIN-B6
PREPARATION OF CRYSTALLINE PHOSPHORYLATED DERIVATIVES OF VITAMIN-B6
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DOI：
10.1021/ja01630a045
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发表时间：
1954-01-01
影响因子：
15
通讯作者：
SOBER, HA
中科院分区：
文献类型：
--
作者：
PETERSON, EA;SOBER, HA
考虑到它们在计划的酶实验中的用途，已经制备了结晶形式的维生素B6的以下衍生物：吡哆胺-5-磷酸、吡哆醛-5-磷酸、吡哆醇-5-磷酸和脱氧吡哆醇-5-磷酸。磷酸化通过加热吡哆胺或脱氧吡哆素与磷酸和五氧化二磷的混合物来完成。以磷酸吡哆胺为原料，经二氧化锰氧化制得磷酸吡哆醛，再经亚硝酸脱氨制得磷酸吡哆辛。在每种情况下，通过弱阳离子交换树脂上的色谱法实现纯化，并在几种溶剂系统中通过纸色谱法进行验证。已经证明了类似的柱程序在将吡哆胺、吡哆醛和吡哆醇的磷酸盐彼此分离以及与其未磷酸化的对应物分离中的有效性。这些化合物的紫外吸收光谱基本上相同，除了磷酸吡哆醛，其区别在于在中性或碱性溶液中在385-390 nm处具有最大吸收，正如其他研究者所报道的那样。这些酯相对耐水解;在冰箱或冰柜中以水溶液储存54天时，很少或没有无机磷酸盐分裂。给出的数据表明它们在25 ℃和100 ℃下在酸和碱中的稳定性。以良好的产率获得纯化合物，范围从磷酸吡哆醛的40%到磷酸脱氧吡哆素的85%。
With a view to their use in projected enzyme experiments, the following derivatives of vitamin B6 have been prepared in crystalline form: pyridoxamine-5-phosphate, pyridoxal-5-phosphate, pyridoxine-5-phosphate and deoxypyridoxine-5-phosphate. Phosphorylation was accomplished by heating pyridoxamine or deoxypyridoxine with a mixture of phosphoric acid and phosphorus pentoxide. Pyridoxal phosphate was prepared by the oxidation of pyridoxamine phosphate with finely divided manganese dioxide at room temperature, and pyridoxine phosphate was obtained from the same compound by deamination with nitrous acid. Purification was achieved in each case by chromatography on a weak cation-exchange resin and verified by paper chromatography in several solvent systems. The effectiveness of a similar column procedure in separating the phosphates of pyridoxamine, pyridoxal and pyridoxine from each other and from their unphosphorylated counterparts has been demonstrated. The ultraviolet absorption spectra of these compounds are essentially identical, with the exception of that of pyridoxal phosphate, which is distinguished by having a maximum at 385-390 ĩ in neutral or alkaline solution, as has been reported by other investigators. These esters are relatively resistant to hydrolysis; little or no inorganic phosphate was split off on storage in aqueous solution in a refrigerator or freezer for 54 days. Data are presented to show their stability in acid and in alkali at 25and 100. The pure compounds were obtained in good yields, ranging from 40% for pyridoxal phosphate to 85% for deoxypyridoxine phosphate.