Berkhout T A, van Amerongen A, Wirtz K W
Eur J Biochem. 1984 Jul 2;142(1):91-7. doi: 10.1111/j.1432-1033.1984.tb08254.x.
The photoactivable glycolipid probes, 2-(4-azido-2-nitrophenoxy)palmitoyl[1-14C]glucosamine (compound A) and 12-(4-azido-2-nitrophenoxy)stearoyl[1-14C]glucosamine (compound B) were synthesized essentially as described before [Iwata, K. K. et al. (1978) Prog. Clin. Biol. Res. 22, 579-589]. These probes were used to label phospholipid vesicles and erythrocyte membranes. A chromatographic method was developed to quantify the individual probe-phospholipid adducts involving both phosphatidylcholine, phosphatidylethanolamine, and phosphatidylserine. For both membranes as well as for both probes a phospholipid labeling pattern was obtained which appeared to reflect the relative content of fatty acid double bonds in each phospholipid class. The distinct labeling of phosphatidylserine in intact erythrocytes strongly suggested that the probes spontaneously and rapidly redistributed between the two halves of the membrane bilayer. In addition, both probes yielded an extensive labeling of the membrane proteins. Analysis by dodecylsulfate-polyacrylamide gel electrophoresis and autoradiography has indicated that the protein labeling pattern was different, depending on whether the 'shallow' probe (compound A) or 'depth' probe (compound B) were used.
可光活化糖脂探针2-(4-叠氮基-2-硝基苯氧基)棕榈酰基[1-¹⁴C]葡糖胺（化合物A）和12-(4-叠氮基-2-硝基苯氧基)硬脂酰基[1-¹⁴C]葡糖胺（化合物B）的合成方法基本如前所述[岩田，K.K.等人（1978年）《临床生物研究进展》22，579 - 589]。这些探针用于标记磷脂囊泡和红细胞膜。开发了一种色谱方法来定量涉及磷脂酰胆碱、磷脂酰乙醇胺和磷脂酰丝氨酸的单个探针 - 磷脂加合物。对于两种膜以及两种探针，均获得了一种磷脂标记模式，该模式似乎反映了每个磷脂类别中脂肪酸双键的相对含量。完整红细胞中磷脂酰丝氨酸的明显标记强烈表明，探针在膜双层的两半之间自发且快速地重新分布。此外，两种探针都对膜蛋白产生了广泛的标记。通过十二烷基硫酸钠 - 聚丙烯酰胺凝胶电泳和放射自显影分析表明，根据使用的是“浅”探针（化合物A）还是“深”探针（化合物B），蛋白质标记模式有所不同。
