Design and synthesis of conformationally constrained glycosylated amino acids.
To probe the conformational requirements of O-linked glycoproteins for binding to various enzymes and receptors, two conformationally constrained glycosylated amino acids, 2 and 3, were designed. The analogues were found to represent two potential low energy conformations of the parent conjugate, 1, by molecular modeling. A convergent synthesis of both 2 and 3 from D-galactose and L-methionine is presented.
Koviach
J L
JL
Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA.
Chappell
M D
MD
Halcomb
R L
RL
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015295:Antigens, Tumor-Associated, Carbohydrate / Q000737:chemistry; D002240:Carbohydrate Sequence; D006023:Glycoproteins / Q000737:chemistry; D006031:Glycosylation; D008958:Models, Molecular; D008969:Molecular Sequence Data; D011487:Protein Conformation
D000596:Amino Acids; D015295:Antigens, Tumor-Associated, Carbohydrate; D006023:Glycoproteins; C055491:sialosyl-Tn antigen