An efficient, scalable synthesis of the molecular transporter octaarginine via a segment doubling strategy
An efficient, scalable synthesis of the molecular transporter octaarginine via a segment doubling strategy
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DOI：
10.1021/ol0161108
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发表时间：
2001-10-18
期刊：
影响因子：
5.2
通讯作者：
VanDeusen, CL
中科院分区：
文献类型：
--
作者：
Wender, PA;Jessop, TC;VanDeusen, CL
精氨酸的短寡聚体作为药物和探针分子进入细胞和组织的非常有效的分子转运体发挥作用。目前，这些化合物通过单向固相合成在树脂上制备。为了扩展这些化合物在治疗和研究应用中的效用，基于片段倍增策略开发了Arg（8）（1）的可扩展的溶液相合成，该策略在13个步骤中进行，从4个步骤的总产率为28%，包括新的一步过脱保护-过胍基化反应。
[GRAPHICS]Short oligomers of arginine function as remarkably efficient molecular transporters of drugs and probe molecules into cells and tissue. Currently, these compounds are prepared on resin through a unidirectional solid-phase synthesis. To extend the utility of these compounds for therapeutic and research applications, a scalable solution-phase synthesis of Arg(8) (1) has been developed on the basis of a segment doubling strategy that proceeds in 13 steps and 28% overall yield from 4, including a novel one-step perdeprotection-perguanidinylation reaction.