TY - JOUR
T1 - Synthesis of Heparan Sulfate- And Dermatan Sulfate-Related Oligosaccharides via Iterative Chemoselective Glycosylation Exploiting Conformationally Disarmed [2.2.2] l -Iduronic Lactone Thioglycosides
AU - Jeanneret, Robin A.
AU - Dalton, Charlotte E.
AU - Gardiner, John M.
PY - 2019/12/6
Y1 - 2019/12/6
N2 - Heparan sulfate (HS) and dermatan sulfate (DS) are l-iduronic acid containing glycosaminoglycans (GAGs) which are implicated in a number of biological processes and conditions including cancer and viral infection. Chemical synthesis of HS and DS is required to generate structurally defined oligosaccharides for a biological study. Herein, we present a new synthetic approach to HS and DS oligosaccharides using chemoselective glycosylation which relies on a disarmed [2.2.2] l-ido lactone motif. The strategy provides a general approach for iterative-reducing end chain extension, using only shelf-stable thioglycoside building blocks, exploiting a conformational switch to control reactivity, and thus requires no anomeric manipulation steps between glycosylations.
AB - Heparan sulfate (HS) and dermatan sulfate (DS) are l-iduronic acid containing glycosaminoglycans (GAGs) which are implicated in a number of biological processes and conditions including cancer and viral infection. Chemical synthesis of HS and DS is required to generate structurally defined oligosaccharides for a biological study. Herein, we present a new synthetic approach to HS and DS oligosaccharides using chemoselective glycosylation which relies on a disarmed [2.2.2] l-ido lactone motif. The strategy provides a general approach for iterative-reducing end chain extension, using only shelf-stable thioglycoside building blocks, exploiting a conformational switch to control reactivity, and thus requires no anomeric manipulation steps between glycosylations.
UR - http://www.scopus.com/inward/record.url?scp=85075155007&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.9b01594
DO - 10.1021/acs.joc.9b01594
M3 - Article (Academic Journal)
C2 - 31674785
AN - SCOPUS:85075155007
SN - 0022-3263
VL - 84
SP - 15063
EP - 15078
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 23
ER -