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偕二全氟叔丁基化β-氨基酸及其保护形式的合成，作为基于肽的药物的潜在药代动力学调节剂和报告分子。

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.

作者信息

Jiang Zhong-Xing, Yu Y Bruce

机构信息

Department of Pharmaceutics and Pharmaceutical Chemistry, College of Pharmacy, University of Utah, Salt Lake City, Utah 84112, USA.

出版信息

J Org Chem. 2007 Feb 16;72(4):1464-7. doi: 10.1021/jo0616308. Epub 2007 Jan 23.

DOI:10.1021/jo0616308
PMID:17243713
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2597546/
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.

摘要

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二全氟叔丁基化β-氨基酸（βFa）及其Fmoc和Boc保护形式。通过标准固相化学将βFa掺入模型三肽中。氨基酸（游离和保护形式）和三肽均显示出尖锐的单峰19F NMR信号。反相色谱法和1-辛醇/水分配测量表明βFa具有极强的疏水性。

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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.偕二全氟叔丁基化β-氨基酸及其保护形式的合成，作为基于肽的药物的潜在药代动力学调节剂和报告分子。
J Org Chem. 2007 Feb 16;72(4):1464-7. doi: 10.1021/jo0616308. Epub 2007 Jan 23.
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引用本文的文献

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Perfluoro-tert-butyl Homoserine Is a Helix-Promoting, Highly Fluorinated, NMR-Sensitive Aliphatic Amino Acid: Detection of the Estrogen Receptor·Coactivator Protein-Protein Interaction by F NMR.全氟叔丁基高丝氨酸是一种促进螺旋形成、高度氟化、对核磁共振敏感的脂肪族氨基酸：通过氟核磁共振检测雌激素受体·共激活因子蛋白-蛋白相互作用。
Biochemistry. 2017 Feb 28;56(8):1062-1074. doi: 10.1021/acs.biochem.6b01020. Epub 2017 Feb 15.
2
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Org Lett. 2016 Dec 16;18(24):6240-6243. doi: 10.1021/acs.orglett.6b02858. Epub 2016 Dec 6.
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本文引用的文献

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(2S,4R)- and (2S,4S)-perfluoro-tert-butyl 4-hydroxyproline: two conformationally distinct proline amino acids for sensitive application in 19F NMR.
(2S,4R)-和(2S,4S)-全氟叔丁基4-羟基脯氨酸：两种构象不同的脯氨酸氨基酸，用于19F核磁共振的灵敏应用。
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Proline editing: a general and practical approach to the synthesis of functionally and structurally diverse peptides. Analysis of steric versus stereoelectronic effects of 4-substituted prolines on conformation within peptides.脯氨酸编辑：一种通用且实用的合成具有不同功能和结构的肽的方法。分析 4-取代脯氨酸在肽中构象上的空间位阻与立体电子效应。
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