Facile solid-phase synthesis of an antifreeze glycoprotein.
The antifreeze glycoproteins (AFGPs) 1 are composed of a repeating tripeptide unit (Ala-Thr-Ala) in which the threonine residue is glycosylated with the disaccharide beta-D-Gal-(1-->3)-alpha-D-GalNAc. A new procedure for synthesizing AFGPs using Fmoc-(Ac4-beta-D-Gal-(1-->3)-benzylidene- alpha-D-GalNAc)Thr-OH (10) as a building block has been developed. Total synthesis of the AFGPs (n = 4, 8) in overall yields of 61% and 33 %, respectively, has demonstrated the usefulness of the method. The synthetic AFGPs 1 (n = 4, 8) showed a similar conformation to the native AFGPs in their circular dichroism spectra.
Tseng
P H
PH
Institute of Biological Chemistry, Academia Sinica, Nankang, Taipei, Taiwan.
Jiaang
W T
WT
Chang
M Y
MY
Chen
S T
ST
D000116:Acetylgalactosamine; D021301:Antifreeze Proteins / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D005690:Galactose; D006031:Glycosylation; D007202:Indicators and Reagents; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D020449:Repetitive Sequences, Amino Acid
D021301:Antifreeze Proteins; D004187:Disaccharides; D007202:Indicators and Reagents; D009842:Oligopeptides; D000116:Acetylgalactosamine; D005690:Galactose