Premium
C‐14 labelling of NVP RAD001—a new rapamycin derivative
Author(s) -
Moenius Th.,
Voges R.,
Mahnke M.,
Burtscher P.,
Metz Y.,
Guenat Ch.
Publication year - 1999
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199901)42:1<29::aid-jlcr164>3.0.co;2-5
Subject(s) - chemistry , labelling , alkylation , derivative (finance) , cyclohexane , stereoselectivity , combinatorial chemistry , organic chemistry , biochemistry , catalysis , financial economics , economics
An optimized fermentation process is described for the carbon‐14 labelling of rapamycin. It is characterized by good reproducibility, high radiochemical purity and excellent yields. L‐[ 14 C 2 ]Pipecolic acid and (1R,3R,4R)‐3,4‐dihydroxyl[1,7‐ 14 C 2 ]cyclohexane carboxylic acid ([ 14 C 2 ]DHCCA) synthesized in an effective stereoselective approach proved to be highly suitable precursors for this purpose. In a final step [ 14 C 4 ]rapamycin was converted by selective C(40)‐O‐alkylation to [ 14 C 4 ]NVP RAD001 , a highly interesting immunosuppressant. Copyright © 1999 John Wiley & Sons, Ltd.