Solid-phase synthesis of a library of functionalized aminodiol scaffolds

✍ Scribed by Peter W. Davis; Stephen A. Osgood; Normand Hébert; Kelly G. Sprankle; Eric E. Swayze

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 223 KB
• Volume: 61
• Category: Article
• ISSN: 0006-3592
• DOI: 10.1002/(sici)1097-0290(1998)61:3<143::aid-cc2>3.0.co;2-o

✦ Synopsis

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.