Insertion of an internal dipeptide into PNA oligomers: thermal melting studies and further functionalization.
Insertion of an internal dipeptide into PNA oligomers: thermal melting studies and further functionalization.
复制标题
将内部二肽插入 PNA 寡聚物：热熔化研究和进一步功能化。
DOI：
10.1016/j.bmcl.2006.02.071
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发表时间：
2006
影响因子：
2.7
通讯作者：
N. Metzler‐Nolte
中科院分区：
文献类型：
--
作者：
Tim Kersebohm;S. Kirin;N. Metzler‐Nolte
采用固相法合成了含有内二肽Gly-Phe的PNA低聚物，并研究了其与互补DNA的相互作用。不同互补DNA序列的紫外吸收熔融实验表明，只有当二肽单元对面没有DNA碱基时，才能获得稳定的PNADNA双链。相反，二肽间隔在双链内形成环状结构。进一步功能化与n -杂环配体描述。在固相合成过程中引入对硝基苯丙氨酸代替苯丙氨酸，随后还原为对氨基苯丙氨酸。与活性酸反应可获得高收率和高纯度的配体偶联物。这一策略为PNA化学中大量的内部取代开辟了一条通用的途径。
The solid phase synthesis of PNA oligomers with the internal dipeptide Gly-Phe is presented and the interaction with complementary DNA investigated. UV absorbance melting experiments with different but complementary DNA sequences show that stable PNADNA duplexes are only obtained when there is no DNA base opposite the dipeptide unit. Instead, the dipeptide spacer forms a loop-like structure within the duplex. Further functionalization with N-heterocyclic ligands is described. p-Nitro-phenylalanine is introduced in place of Phe during solid phase synthesis and subsequently reduced to p-amino-phenylalanine. Reaction with activated acids provides the ligand conjugates in high yield and purity. This strategy opens a universal route to a large number of internal substitutions in PNA chemistry.