Tetrahydrofuran-based amino acids as library scaffolds.
A furanose sugar amino acid (SAA) has been utilized as a library scaffold for the first time. Two furanose SAA scaffolds were examined to illustrate their potential for derivatization. The resulting 99-member library contained three orthogonal points of diversification that allowed easy access to ethers and carbamates from a hydroxyl moiety, a range of ureas from an azide (via an amine), and a range of amides from a methyl ester. The novel amide formation (by displacement of the methoxide from the methyl ester moiety) was achieved in good yield and purity with high structural confidence. Full characterization of several library intermediates (including a crystal structure) was obtained. The library was submitted for antibacterial screening.
Dyson Perrins Laboratory, Oxford Centre for Molecular Sciences, University of Oxford, South Parks Road, Oxford OX1 3QY, U.K.
Alison A
AA
Edwards
Osamu
O
Ichihara
Stephen
S
Murfin
Robin
R
Wilkes
Mark
M
Whittaker
David J
DJ
Watkin
George W J
GW
Fleet
D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D001386:Azides / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry; D019281:Dimerization; D004987:Ethers / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D008956:Models, Chemical; D013400:Sugar Acids / Q000737:chemistry
D000577:Amides; D000596:Amino Acids; D001386:Azides; D002219:Carbamates; D004987:Ethers; D005663:Furans; D013400:Sugar Acids; C018674:tetrahydrofuran