TY - JOUR
T1 - Chemo-enzymatic synthesis of C-9 acetylated sialosides
AU - Rauvolfova, Jana
AU - Venot, Andre
AU - Boons, Geert-Jan
PY - 2008
Y1 - 2008
N2 - A chemo-enzymatic synthesis of [(5-acetamido-9-O-acetyl-3,5-dideoxy-d-glycero-α-d-galacto-2-nonulopyranosylonic acid)-(2→3)-O-(β-d-galactopyranosyl)-(1→3)-O-(2-acetamido-2-deoxy-α-d-galactopyranosyl)]-l-serine acetate (1) has been accomplished by a regioselective chemical acetylation of Neu5Ac (2) to give 9-O-acetylated sialic acid 3, which was enzymatically converted into CMP-Neu5,9Ac2 (4) employing a recombinant CMP-sialic acid synthetase from Neisseria meningitis [EC 2.7.7.43]. The resulting compound was then employed for the enzymatic glycosylation of the C-3′ hydroxyl of chemically prepared glycosylated amino acid 10 using recombinant rat α-(2→3)-O-sialyltransferase expressed in Spodooptera frugiperda [EC 2.4.99.4] to give, after deprotection of the Nα-benzyloxycarbonyl (CBz)-protecting group of serine, target compound 1. The Nα-CBz-protected intermediate 11 can be employed for the synthesis of glycolipopeptides for immunization purposes.
AB - A chemo-enzymatic synthesis of [(5-acetamido-9-O-acetyl-3,5-dideoxy-d-glycero-α-d-galacto-2-nonulopyranosylonic acid)-(2→3)-O-(β-d-galactopyranosyl)-(1→3)-O-(2-acetamido-2-deoxy-α-d-galactopyranosyl)]-l-serine acetate (1) has been accomplished by a regioselective chemical acetylation of Neu5Ac (2) to give 9-O-acetylated sialic acid 3, which was enzymatically converted into CMP-Neu5,9Ac2 (4) employing a recombinant CMP-sialic acid synthetase from Neisseria meningitis [EC 2.7.7.43]. The resulting compound was then employed for the enzymatic glycosylation of the C-3′ hydroxyl of chemically prepared glycosylated amino acid 10 using recombinant rat α-(2→3)-O-sialyltransferase expressed in Spodooptera frugiperda [EC 2.4.99.4] to give, after deprotection of the Nα-benzyloxycarbonyl (CBz)-protecting group of serine, target compound 1. The Nα-CBz-protected intermediate 11 can be employed for the synthesis of glycolipopeptides for immunization purposes.
UR - http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=ORCID&SrcApp=OrcidOrg&DestLinkType=FullRecord&DestApp=WOS_CPL&KeyUT=WOS:000257657500009&KeyUID=WOS:000257657500009
U2 - 10.1016/j.carres.2008.05.002
DO - 10.1016/j.carres.2008.05.002
M3 - Article
SN - 0008-6215
VL - 343
SP - 1605
EP - 1611
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - 10-11
ER -