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 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.
Guisado
Cristina
C
IC-Vec Ltd., Flowers Building, Armstrong Road, London SW7 2AZ, UK.
Waterhouse
Jodie E
JE
Price
Wayne S
WS
Jorgensen
Michael R
MR
Miller
Andrew D
AD
D000588:Amines / Q000138:chemical synthesis*; D016503:Drug Delivery Systems; D016023:Integrins / Q000378:metabolism*; D008051:Lipid Bilayers / Q000737:chemistry* / Q000378:metabolism; D008168:Lung / Q000187:drug effects*; D010446:Peptide Fragments / Q000138:chemical synthesis* / Q000378:metabolism; D012137:Respiratory System / Q000187:drug effects*
D000588:Amines; D016023:Integrins; D008051:Lipid Bilayers; D010446:Peptide Fragments; C113256:integrin alpha 9 beta 1