Synthesis of N4-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine analogues. n-Butyramide, 3-chloropropionamide, 3-aminopropionamide, and isovaleramide analogues.
The syntheses of four analogues of N4-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine are described. Activated carboxylic acids were reacted with 2-acetamido-2-deoxy-beta-D-glucopyranosylamine. n-Butyric anhydride gave N-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-n-butyramide. 3-Chloropropionic anhydride was synthesized from 3-chloropropionic acid and gave N-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-3-chloropropionamide. Equilibration of the latter with ammonium bicarbonate gave N1-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-3-aminopropionamide. Succinimidyl isovalerate was synthesized and gave N-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-isovaleramide.
Kaylor
J J
JJ
Department of Chemistry, The University of North Carolina at Charlotte, 28223-0001, USA.
Risley
J M
JM
D000117:Acetylglucosamine / Q000031:analogs & derivatives / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D001227:Aspartylglucosylaminase / Q000378:metabolism; D002087:Butyrates / Q000737:chemistry; D045782:Hemiterpenes; D010421:Pentanoic Acids / Q000737:chemistry; D011422:Propionates / Q000737:chemistry*; D015091:beta-Alanine / Q000031:analogs & derivatives* / Q000737:chemistry
C438086:3-chloropropionamide; D000577:Amides; D002087:Butyrates; D045782:Hemiterpenes; D010421:Pentanoic Acids; D011422:Propionates; D015091:beta-Alanine; C008216:isovaleric acid; C000009:N-acetylglucosaminylasparagine; C012731:beta-alanine amide; C038165:isovaleramide; C006866:butyramide; D001227:Aspartylglucosylaminase; D000117:Acetylglucosamine