Fluorous-assisted chemoenzymatic synthesis of heparan sulfate oligosaccharides.
The chemoenzymatic synthesis of heparan sulfate tetrasaccharide (1) and hexasaccharide (2) with a fluorous tag attached at the reducing end is reported. The fluorous tert-butyl dicarbonate ((F)Boc) tag did not interfere with enzymatic recognition for both elongation and specific sulfation, and flash purification was performed by standard fluorous solid-phase extraction (FSPE). Based on an (F)Boc attached disaccharide as acceptor, a series of partial N-sulfated, 6-O-sulfated heparan sulfate oligosaccharides were successfully synthesized employing fluorous techniques.
Department of Chemistry and Chemical Biology, ‡Department of Biology, and §Departments of Chemical and Biological Engineering and Biomedical Engineering, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute , Troy, New York 12180, United States.
Chao
C
Cai
Demetria M
DM
Dickinson
Lingyun
L
Li
Sayaka
S
Masuko
Matt
M
Suflita
Victor
V
Schultz
Shawn D
SD
Nelson
Ujjwal
U
Bhaskar
Jian
J
Liu
Robert J
RJ
Linhardt
D002625:Chemistry, Organic / Q000379:methods; D016695:Glycosyltransferases / Q000378:metabolism; D006497:Heparan Sulfate / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D052616:Solid Phase Extraction
D016695:Glycosyltransferases; D006497:Heparan Sulfate; D009844:Oligosaccharides