Chemo-enzymatic synthesis of trimeric sialyl Lewis(x) pentadecasaccharide

The enzymatic synthesis of trimeric sialyl Lewis(x) pentadecasaccharide (6), a 15-mer, from a trimannoside precursor required six different glycosyltransferase enzymes and four nucleotide donor sugars. Three N-acetylglucosaminyl residues were transferred from UDP-N-acetylglucosamine to a trimannosid...

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Bibliographic Details
Published inCanadian journal of chemistry Vol. 80; no. 6; pp. 540 - 545
Main Authors Liu, YC, Li, H, Otter, A, Kamath, VP, Streiff, MB, Palcic, MM
Format Journal Article
LanguageEnglish
Published OTTAWA Canadian Science Publishing 01.06.2002
Canadian Science Publishing NRC Research Press
Subjects
Chemistry
Chemistry, Multidisciplinary
Enzymes
Physical Sciences
Science & Technology
Sugar
sialyl Lewis(x)
glycosyltransferases
ASSAY
AFFINITY
CATALYZED SYNTHESIS
LIVER
pentadecasaccharide
BINDING
N-ACETYLGLUCOSAMINYLTRANSFERASE-I
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Summary:The enzymatic synthesis of trimeric sialyl Lewis(x) pentadecasaccharide (6), a 15-mer, from a trimannoside precursor required six different glycosyltransferase enzymes and four nucleotide donor sugars. Three N-acetylglucosaminyl residues were transferred from UDP-N-acetylglucosamine to a trimannoside by N-acetylglucosaminyltransferases I, II, and V, respectively. Galactosylation using beta(1-->4) galactosyltransferase and UDP-galactose gave three N-acetyl-lactosamine units in nonasaccharide 4. Sialylation of 4 with alpha(2-->3) sialyltransferase and CMP-N-acetylneuraminic acid was followed by fucosylation with alpha(1-->3) fucosyltransferase and GDP-fucose giving the 15-mer 6 in mg quantities. Compound 4 was also converted to a trimeric Lewis(x) dodecasaccharide 12-mer with alpha(1-->3) fucosyltransferase and GDP-fucose and to a trimeric alpha-2,6-sialyl N-acetyllactosamine dodecasaccharide 12-mer with alpha(2-->6) sialyltransferase and CMP-N-acetylneuraminic acid.
ISSN:0008-4042
1480-3291
DOI:10.1139/V02-073