Comparison of disaccharide donors for heparan sulfate synthesis: uronic acids vs. their pyranose equivalents.
Org Biomol Chem
; 18(25): 4728-4733, 2020 07 01.
Article
in En
| MEDLINE
| ID: mdl-32531013
ABSTRACT
Late oxidation of hexose based building blocks or the use of uronic acid containing building blocks are two complementary strategies in the synthesis of glycosaminoglycans, the latter simplifiying the later stages of the process. Here we report the synthesis and evaluation of various disaccharide donors-uronic acids and their pyranose equivalents-for the synthesis of heparan sulfate, using an established protective group strategy. Hexose based "imidate" type donors perform well in the studied glycosylations, while their corresponding uronate esters fall short; a uronate ester thioglycoside performs equal to, if not better than, a hexose thioglycoside equivalent.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Org Biomol Chem
Journal subject:
BIOQUIMICA
/
QUIMICA
Year:
2020
Type:
Article
Affiliation country:
New Zealand