Chemoenzymatic synthesis of 3'-O-(carboxyalkyl)fluorescein labels.
A general and versatile method is described for the synthesis of fluorescent labels. Coupling of the 3'-phenol of fluorescein methyl ester with hydroxyalkyl benzyl esters, followed by benzyl ester hydrolysis, provided a series of fluorescein carboxyalkyl ethers. Use of the Mitsunobu reaction allowed for the introduction of linkers of different lengths onto the 3'-phenol of fluorescein. Chemoenzymatic benzyl ester hydrolysis was achieved with LPL-80 lipase, providing pH-independent labels useful for the preparation of fluorescent conjugates.
Adamczyk
M
M
Department of Chemistry (D9NM), Abbott Laboratories, Building AP 20, 100 Abbott Park Road, Abbott Park, Illinois, 60064-6016, USA. maciej.adamczyk@abbott.com
Grote
J
J
Moore
J A
JA
D005452:Fluoresceins / Q000138:chemical synthesis* / Q000737:chemistry; D006863:Hydrogen-Ion Concentration
D005452:Fluoresceins