Premium
Facile Solid‐Phase Synthesis of an Antifreeze Glycoprotein
Author(s) -
Tseng PingHui,
Jiaang WeirTorn,
Chang MengYang,
Chen ShuiTein
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20010202)7:3<585::aid-chem585>3.0.co;2-6
Subject(s) - tripeptide , disaccharide , chemistry , glycoprotein , circular dichroism , antifreeze , threonine , stereochemistry , residue (chemistry) , biochemistry , peptide , serine , organic chemistry , enzyme
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 β ‐ D ‐Gal‐(1→3)‐ α ‐ D ‐GalNAc. A new procedure for synthesizing AFGPs using Fmoc‐(Ac 4 ‐ β ‐ D ‐Gal‐(1→3)‐benzylidene‐ α ‐ 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.