DIAZO-FUNCTIONALIZED AND AZIDO-FUNCTIONALIZED GLUTARALDEHYDES AS CROSS-LINKING REAGENTS AND POTENTIAL FIXATIVES FOR ELECTRON-MICROSCOPY

被引:38
作者
CAI, SX [1 ]
KEANA, JFW [1 ]
机构
[1] UNIV OREGON, DEPT CHEM, EUGENE, OR 97403 USA
关键词
D O I
10.1021/bc00007a007
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
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.
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页码:38 / 43
页数:6
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