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The synthesis of a geminally perfluoro-tert-butylated beta-amino acid and its protected forms as a potential pharmacokinetic modulator and reporter for peptide-based pharmaceuticals.

ABSTRACT: To modulate and report the pharmacokinetics of peptide-based pharmaceuticals, a novel geminally perfluoro-tert-butylated beta-amino acid (betaFa) and its Fmoc- and Boc-protected forms were designed and synthesized. betaFa 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 19F NMR signal. Reversed-phase chromatography and 1-octanol/water partition measurements demonstrate that betaFa is extremely hydrophobic.

SUBMITTER: Jiang ZX

PROVIDER: S-EPMC2597546 | biostudies-literature | 2007 Feb

REPOSITORIES: biostudies-literature

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The synthesis of a geminally perfluoro-tert-butylated beta-amino acid and its protected forms as a potential pharmacokinetic modulator and reporter for peptide-based pharmaceuticals.

Jiang Zhong-Xing ZX Yu Y Bruce YB

The Journal of organic chemistry 20070123 4

To modulate and report the pharmacokinetics of peptide-based pharmaceuticals, a novel geminally perfluoro-tert-butylated beta-amino acid (betaFa) and its Fmoc- and Boc-protected forms were designed and synthesized. betaFa 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 19F NMR signal. Reversed-phase chromatography and 1-octanol/water partition measurements demonstrate that betaFa is extr ...[more]

PMID: 17243713

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