The synthesis of a geminally perfluoro-tert-butylated β-amino acid and its protected forms as a potential pharmacokinetic modulator and reporter for peptide-based pharmaceuticals
The synthesis of a geminally perfluoro-tert-butylated β-amino acid and its protected forms as a potential pharmacokinetic modulator and reporter for peptide-based pharmaceuticals
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DOI：
10.1021/jo0616308
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发表时间：
2007-02-16
影响因子：
3.6
通讯作者：
Yu, Y. Bruce
中科院分区：
文献类型：
--
作者：
Jiang, Zhong-Xing;Yu, Y. Bruce
为了调节和报告基于肽的药物的药代动力学，设计并合成了一种新型的偕全氟叔丁基化β-氨基酸（β Fa）及其Fmoc和Boc保护形式。通过标准固相化学将β Fa掺入模型三肽中。氨基酸（游离的和受保护的）和三肽都显示出尖锐的单线态F-19 NMR信号。反相色谱和1-辛醇/水分配测量表明，β Fa是非常疏水的。
To modulate and report the pharmacokinetics of peptide-based pharmaceuticals, a novel geminally perfluoro-tert-butylated beta-amino acid (beta Fa) and its Fmoc- and Boc-protected forms were designed and synthesized. beta Fa was incorporated into a model tripeptide via standard solid-phase chemistry. Both the amino acid (free and protected) and the tripeptide show a sharp singlet F-19 NMR signal. Reversed-phase chromatography and 1-octanol/water partition measurements demonstrate that beta Fa is extremely hydrophobic.