Solid-phase synthesis of a library of functionalized aminodiol scaffolds.
A combinatorial library motif has been developed based on orthogonally protected aminodiol scaffolds. Amine functionality was derivatized by commercially available electrophiles including carboxylic acids, sulfonyl chlorides, isocyanates, and aldehydes. A hydroxyl moiety was converted to a carbamate linkage, allowing a variety of amines to be incorporated. The scaffold was anchored to TentaGel at the second hydroxyl via a succinyl linker, which was hydrolyzed by mild aqueous basic conditions. The method was used to make a library of about 17,000 different members in mixtures of 5 per sample.
Davis
P W
PW
Ibis Therapeutics, a Division of Isis Pharmaceuticals, 2292 Faraday Avenue, Carlsbad, California 92008, USA.
Osgood
S A
SA
Hébert
N
N
Sprankle
K G
KG
Swayze
E E
EE
D000438:Alcohols / Q000138:chemical synthesis*; D000473:Alkanes / Q000138:chemical synthesis; D000588:Amines / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D013058:Mass Spectrometry; D008722:Methods; D008956:Models, Chemical; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis; D011392:Proline / Q000031:analogs & derivatives; D012117:Resins, Synthetic
D000438:Alcohols; D000473:Alkanes; D000588:Amines; D007202:Indicators and Reagents; D010880:Piperidines; D012117:Resins, Synthetic; D011392:Proline