Cai S X, Keana J F
Department of Chemistry, University of Oregon, Eugene 97403.
Bioconjug Chem. 1991 Jan-Feb;2(1):38-43. doi: 10.1021/bc00007a007.
The synthesis of diazo and perfluorophenyl azide (PFPA) functionalized glutaraldehydes 7 and 13a-d as new cross-linking reagents for bioconjugation and potential fixatives for electron microscopy is reported. A key step is the generation of the 1,5-dialdehyde structures by oxidative cleavage of the corresponding cyclopentene epoxide using HIO4 in aqueous tetrahydrofuran. A model reaction between 3-substituted glutaraldehyde 14 and 6-aminohexanoic acid resulted in the formation of pyridinium ion containing products with UV spectra comparable to those observed with glutaraldehyde itself. Thus modification of glutaraldehyde in the 3-position most probably did not significantly change its reactivity with amines under chemical-fixation conditions. Fixation of red blood cells by 7 demonstrates that as a fixative, 7 is comparable to glutaraldehyde.
报道了重氮和全氟苯基叠氮化物（PFPA）功能化戊二醛7和13a - d的合成，它们作为用于生物共轭的新型交联试剂和电子显微镜的潜在固定剂。关键步骤是在水 - 四氢呋喃中使用高碘酸通过相应环戊烯环氧化物的氧化裂解生成1,5 - 二醛结构。3 - 取代戊二醛14与6 - 氨基己酸之间的模型反应导致形成含吡啶鎓离子的产物，其紫外光谱与戊二醛本身观察到的光谱相当。因此，在化学固定条件下，3 - 位戊二醛的修饰很可能不会显著改变其与胺的反应性。用7固定红细胞表明，作为固定剂，7与戊二醛相当。
