Synthesis of sulfonamide-conjugated glycosyl-amino acid building blocks.
The efficient synthesis of novel glycoconjugate amino acid building blocks wherein the amino acid and carbohydrate moieties are linked via a sulfonamide functional group is reported. The general reaction sequence consists of coupling a glycosyl thioacetate to an amino acid methyl ester followed by oxidation and deprotection of the carbohydrate moiety. We demonstrate the synthesis of derivatives from a range of amino acids, with reaction at either the α-amino group of amino acid precursors or the sidechain ε-amino group of lysine precursors.
Eskitis Institute for Drug Discovery, Griffith University, Brisbane, Queensland 4111, Australia.
Marie
M
Lopez
Eskitis Institute for Drug Discovery, Griffith University, Brisbane, Queensland 4111, Australia.
Laurent F
LF
Bornaghi
Eskitis Institute for Drug Discovery, Griffith University, Brisbane, Queensland 4111, Australia. Electronic address: s.poulsen@griffith.edu.au.
Sally-Ann
SA
Poulsen
D000107:Acetylation; D000596:Amino Acids / Q000138:chemical synthesis*; D006020:Glycopeptides / Q000138:chemical synthesis*; D006031:Glycosylation; D013449:Sulfonamides / Q000737:chemistry
D000596:Amino Acids; D006020:Glycopeptides; D013449:Sulfonamides
Carbohydrate; Chemical biology; Deacetylation; Glycopeptide; Isostere; Peptidomimetic