Synthesis of multiantennary complex type N-glycans by use of modular building blocks.
A modular set of oligosaccharide building blocks was developed for the synthesis of multiantennary N-glycans of the complex type, which are commonly found on glycoproteins. The donor building blocks were laid out for the elongation of a core trisaccharide acceptor (beta-mannosyl chitobiose) conveniently protected with a single benzylidene moiety at the beta-mannoside. Through two consecutive regio- and stereoselective couplings the donors gave N-glycans with three to five antennae in high yields. Due to the consistent protection group pattern of the donors the deprotection of the final products can be performed by using a general reaction sequence.
Unverzagt
Carlo
C
Bioorganische Chemie, Universität Bayreuth, Gebäude NW1, 95440 Bayreuth, Germany. carlo.unverzagt@uni-bayreuth.de
Gundel
Gislinde
G
Eller
Steffen
S
Schuberth
Ralf
R
Seifert
Joachim
J
Weiss
Harald
H
Niemietz
Mathäus
M
Pischl
Matthias
M
Raps
Claudia
C
D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry; D006023:Glycoproteins / Q000138:chemical synthesis / Q000737:chemistry; D008362:Mannosides / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000737:chemistry
D004187:Disaccharides; D006023:Glycoproteins; D008362:Mannosides; D009844:Oligosaccharides; D011134:Polysaccharides; C032438:chitobiose