The facile preparation of primary and secondary amines via an improved Fukuyama-Mitsunobu procedure. Application to the synthesis of a lung-targeted gene delivery agent

An efficient modification of the Fukuyama-Mitsunobu procedure has been developed whereby primary or secondary amines can be synthesized from alkyl alcohols and the corresponding nosyl-protected/activated amine. Most importantly, the use of the DTBAD and diphenylpyridinylphosphine, as Mitsunobu reage...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2005-03, Vol.3 (6), p.1049-1057
Main Authors: Guisado, Cristina, Waterhouse, Jodie E, Price, Wayne S, Jorgensen, Michael R, Miller, Andrew D
Format: Article
Language:English
Subjects:
Amines - chemical synthesis
Drug Delivery Systems
Integrins - metabolism
Lipid Bilayers - chemistry
Lipid Bilayers - metabolism
Lung - drug effects
Peptide Fragments - chemical synthesis
Peptide Fragments - metabolism
Respiratory System - drug effects
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Summary:An efficient modification of the Fukuyama-Mitsunobu procedure has been developed whereby primary or secondary amines can be synthesized from alkyl alcohols and the corresponding nosyl-protected/activated amine. Most importantly, the use of the DTBAD and diphenylpyridinylphosphine, as Mitsunobu reagents, generates reaction by-products that can be easily removed, providing a remarkably clean product mixture. This improved technique was implemented in the synthesis of a complex lipopeptide designed to target alpha9beta1-integrin proteins predominant on upper airway epithelial cells.
ISSN:1477-0520
1477-0539
DOI:10.1039/b418168a