Sloop F V, Brown G M, Foote R S, Jacobson K B, Sachleben R A
Biology Division, Oak Ridge National Laboratory, Tennessee 37831.
Bioconjug Chem. 1993 Sep-Oct;4(5):406-9. doi: 10.1021/bc00023a017.
The synthesis of 3-(triethylstannyl)propanoic acid (TESPA), an organometallic reporter group that enables the mass labeling of oligonucleotides with stable isotopes of tin, is described. Synthesized from commercially available isotopically-enriched SnO2 in a five step process, the NHS ester of TESPA is produced with an overall yield of 40%. This simplification of the standard synthetic scheme, with two less synthetic steps and a coincident 60% yield increase, is accomplished through the use of the reagent N-(acryloxy)succinimide and the free radical initiator AMPN. The conditions for the attachment of the reporter group to priming oligonucleotides and the subsequent HPLC isolation of the labeled primers are also detailed.
本文描述了3-(三乙基锡烷基)丙酸(TESPA)的合成，这是一种有机金属报告基团，可用于用锡的稳定同位素对寡核苷酸进行大规模标记。TESPA由市售的同位素富集SnO₂通过五步反应合成，其NHS酯的总产率为40%。通过使用试剂N-(丙烯酰氧基)琥珀酰亚胺和自由基引发剂AMPN，简化了标准合成方案，减少了两步合成步骤，同时产率提高了60%。还详细介绍了报告基团与引物寡核苷酸连接的条件以及随后通过HPLC分离标记引物的方法。
