Sonogashira and "Click" reactions for the N-terminal and side-chain functionalization of peptides with [Mn(CO)3(tpm)]+-based CO releasing molecules (tpm = tris(pyrazolyl)methane)
Sonogashira and "Click" reactions for the N-terminal and side-chain functionalization of peptides with [Mn(CO)3(tpm)]+-based CO releasing molecules (tpm = tris(pyrazolyl)methane)
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DOI：
10.1039/b819091g
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发表时间：
2009-01-01
影响因子：
4
通讯作者：
Schatzschneider, Ulrich
中科院分区：
文献类型：
--
作者：
Pfeiffer, Hendrik;Rojas, Alfonso;Schatzschneider, Ulrich
通过Pd催化的Sonogashira交叉偶联反应和炔叠氮基1，3-偶极环加成反应(Click反应)，将一种新发现的基于[Mn(CO)(3)(TPM)](+)的可光激活CO释放分子(CORM)偶联到功能化氨基酸和模型肽上。两者都被发现与存在的所有官能团完全相容。红外光谱、电喷雾质谱、反相高效液相色谱检测结果表明，球茎-多肽结合物的纯度高、产率高。肌红蛋白分析表明，它们具有与母体化合物相同的CO释放特性。因此，这项工作为将球茎定向输送到细胞系统开辟了道路。
A recently identified photoactivatable CO releasing molecule (CORM) based on [Mn(CO)(3)(tpm)](+) was conjugated to functionalized amino acids and model peptides using the Pd-catalyzed Sonogashira cross-coupling and the alkyne-azid 1,3-dipolar cycloaddition ("Click reaction"). Both were found to be fully compatible with all functional groups present. The CORM-peptide conjugates were isolated in reasonable yield and high purity, as indicated by IR spectroscopy, ESI mass spectrometry and RP-HPLC. The myoglobin assay was used to demonstrate that they have CO release properties identical those of the parent compound. This work thus opens the way for a targeted delivery of CORMs to cellular systems.