Chemo-enzymatic synthesis of glycopolymers and sequential glycopeptides bearing lactosamine and sialyl Lewisx unit pendant chains

Enzymatic synthesis of N-linked oligosaccharides terminating in multiple sialyl-Lewisx and GalNAc-Lewisx determinants: clustered glycosides for studying selectin interactions

Carbohydrate Research ◽

10.1016/s0008-6215(97)10098-2 ◽

1998 ◽

Vol 306 (3) ◽

pp. 387-400 ◽

Cited By ~ 14

Author(s):

V.Hayden Thomas ◽

Jordan Elhalabi ◽

Kevin G Rice

Keyword(s):

Enzymatic Synthesis ◽

Sialyl Lewisx

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Substrate specificity of fucosyl transferase III: An efficient synthesis of sialyl Lewisx-, sialyl Lewisa-derivatives and mimetics thereof

Canadian Journal of Chemistry ◽

10.1139/v00-081 ◽

2000 ◽

Vol 78 (6) ◽

pp. 892-904 ◽

Cited By ~ 9

Author(s):

Beat Ernst ◽

Bea Wagner ◽

Gabi Baisch ◽

Andreas Katopodis ◽

Tammo Winkler ◽

...

Keyword(s):

Substrate Specificity ◽

Enzymatic Synthesis ◽

Reaction Rates ◽

Efficient Synthesis ◽

Natural Substrate ◽

Sialyl Lewisx ◽

Sialyl Lewis ◽

Sialyl Lewisa

Fucosyl transferase III (FucT III) has previously been characterized as the most general enzyme of the FucT family, as judged from its ability to catalyze the transfer of fucose to both Galβ(1-3)GlcNAc and Galβ(1-4)GlcNAc. In order to explore the synthetic potential of FucT III for the enzymatic synthesis of sialyl Lewisx and sialyl Lewisa derivatives, its substrate specificity has been probed using a number of natural substrate mimetics. A remarkable range of acceptor substrates was found when N-acetyl glucosamine was replaced by D-glucal, (R,R)-1,2-cyclohexanediol and (R,R)-butan-2,3-diol. Although the reaction rates were low compared to the reaction with the natural substrates, they proved to be sufficient for the synthesis of preparative amounts.Key words: fucosyl transferase III, sialyl Lewisa, sialyl Lewisx, carbohydrate mimetics.

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ChemInform Abstract: Chemo-enzymatic Synthesis of Trimeric Sialyl Lewisx Pentadecasaccharide.

ChemInform ◽

10.1002/chin.200245183 ◽

2010 ◽

Vol 33 (45) ◽

pp. no-no

Author(s):

Yeuk Chuen Liu ◽

Hong Li ◽

Albin Otter ◽

Vivekanand P. Kamath ◽

Markus B. Streiff ◽

...

Keyword(s):

Enzymatic Synthesis ◽

Sialyl Lewisx

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Chemo-enzymatic synthesis of trimeric sialyl Lewisx pentadecasaccharide

Canadian Journal of Chemistry ◽

10.1139/v02-073 ◽

2002 ◽

Vol 80 (6) ◽

pp. 540-545 ◽

Cited By ~ 7

Author(s):

Yeuk Chuen Liu ◽

Hong Li ◽

Albin Otter ◽

Vivekanand P Kamath ◽

Markus B Streiff ◽

...

Keyword(s):

Key Words ◽

Enzymatic Synthesis ◽

Sialyl Lewisx ◽

Acetylneuraminic Acid ◽

Sialyl Lewis

The enzymatic synthesis of trimeric sialyl Lewisx 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 Lewisx 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 Lewisx.

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