A new approach to the neoglycopeptides: synthesis of urea- and carbamate-tethered N-acetyl-D-glucosamine amino acid conjugates.
A novel approach to the synthesis of Fmoc-protected neoglycopeptide building blocks is described. Oxidation of N-acetyl-D-glucosamine isonitrile afforded the corresponding highly reactive glycopyranosyl isocyanate, which reacted with amino acid derivatives to furnish the corresponding urea- and carbamate-tethered Fmoc-protected N-acetyl-D-glucosamine amino acid conjugates in good yields. [reaction: see text]
Ichikawa
Yoshiyasu
Y
Faculty of Science, Kochi University, Akebono-cho, Kochi 780-8520, Japan. ichikawa@kochi-u.ac.jp
Ohara
Fumiyo
F
Kotsuki
Hiyoshizo
H
Nakano
Keiji
K
D000596:Amino Acids / Q000737:chemistry*; D002219:Carbamates / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D014508:Urea / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D000596:Amino Acids; D002219:Carbamates; D006020:Glycopeptides; D014508:Urea; D005944:Glucosamine