Chemo-enzymatic synthesis of trimeric sialyl Lewis x pentadecasaccharide

• Published in: Canadian journal of chemistry Vol. 80; no. 6; pp. 540 - 545
• Main Authors: Liu, Yeuk Chuen, Li, Hong, Otter, Albin, Kamath, Vivekanand P, Streiff, Markus B, Palcic, Monica M
• Format: Journal Article
• Language: English
• Published: 01.06.2002
• ISSN: 0008-4042; 1480-3291
• DOI: 10.1139/v02-073

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 β(1[Formula: see text]4) galactosyltransferase and UDP-galactose gave three N-acetyl lactosamine units in nonasaccharide 4. Sialylation of 4 with α(2[Formula: see text]3) sialyltransferase and CMP-N-acetylneuraminic acid was followed by fucosylation with α(1[Formula: see text]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 α(1[Formula: see text]3) fucosyltransferase and GDP-fucose and to a trimeric α-2,6-sialyl N-acetyllactosamine dodecasaccharide 12-mer with α(2[Formula: see text]6) sialyltransferase and CMP-N-acetylneuraminic acid. Key words: glycosyltransferases, pentadecasaccharide, sialyl Lewis x .