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Zeng, Steffen; Gallego, Ricardo Gutiérrez; Dinter, André; Malissard, Martine; Kamerling, Johannis P.; Vliegenthart, Johannes F.G.; Berger, Eric G.

doi:10.1023/a:1007065803554

Cited by 14 publications

(2 citation statements)

References 58 publications

(63 reference statements)

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“…The N -terminal glycosulfopeptide of PGSL-1 has been obtained by chemoenzymatic approaches. ,, In these procedures, a glycosulfopeptide that contains an N -acetyl galactosamine linked to a threonine moiety was chemically assembled. Subsequently, glycosyl transferases were employed to assemble the complete oligosaccharide.…”

Section: Introductionmentioning

confidence: 99%

Rapid Assembly of Oligosaccharides: A Highly Convergent Strategy for the Assembly of a Glycosylated Amino Acid Derived from PSGL-1

Vohra¹,

Buskas²,

Boons³

2009

J. Org. Chem.

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P-selectin and P-selectin glycoprotein ligand 1 (PSGL-1) are vascular adhesion molecules that play an important role in the recruitment of leukocytes to inflamed tissue by establishing leukocyteendothelial and leukocyte-platelet interaction. P-selectin binds to the amino-terminus of PSGL-1 through recognition of a sialyl Lewis x (SLe x ) moiety linked to a properly positioned core-2 O-glycan and three tyrosine sulfate residues. We have developed a highly convergent synthesis of the PSGL-1 oligosaccharide linked to threonine based on the use of trichoroacetimidate donors and thioglycosyl acceptors that give products that can immediately be employed in a subsequent glycosylation step without the need for protecting group manipulations. Furthermore, by employing one-pot multi-step glycosylation sequences the number of purification steps could be minimized. The process of oligosaccharide assembly was further streamlined by combining protecting group manipulations and glycosylations as one-pot multi-step synthetic procedure. The resulting PSGL-1 oligosaccharide is properly protected for glycopeptide assembly. It is to be expected that the strategic principles employed for the synthesis of the target compound can be applied for the preparation of other complex oligosaccharides of biological and medical importance.

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Section: Introductionmentioning

confidence: 99%

Rapid Assembly of Oligosaccharides: A Highly Convergent Strategy for the Assembly of a Glycosylated Amino Acid Derived from PSGL-1

Vohra¹,

Buskas²,

Boons³

2009

J. Org. Chem.

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“…Fucose is the component of Sialyl Lewis X and some cancer associated antigens, such as PSGL-1 [92,93]. A working GDP-Man and GDP-Fuc regeneration cycle will allow us to achieve a more ambitious goal of synthesizing different lengths of N-glycans and cancerassociated carbohydrate antigens.…”

Section: Regeneration Systems For Gdp-man and Gdp-fucmentioning

confidence: 99%

Enzymatic Biosynthesis of Oligosaccharides and Glycoconjugates

Song¹,

Zhang²,

Li³

et al. 2006

COS

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Natural carbohydrates have complex structures including many kinds of monosaccharide units, which are very difficult and costly to generate by chemical synthetic approaches. Over the years, enzymatic approaches have been gaining popularity for the synthesis of oligosaccharides and glycoconjugates, and it is becoming increasingly feasible to produce complex carbohydrates in large scale, following enzymatic biosynthetic pathways.

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update covering the period 1999–2000

Harvey

2006

Mass Spectrometry Reviews

125

112

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This review describes the use of matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of carbohydrates and glycoconjugates and continues coverage of the field from the previous review published in 1999 (D. J. Harvey, Matrix-assisted laser desorption/ionization mass spectrometry of carbohydrates, 1999, Mass Spectrom Rev, 18:349-451) for the period 1999-2000. As MALDI mass spectrometry is acquiring the status of a mature technique in this field, there has been a greater emphasis on applications rather than to method development as opposed to the previous review. The present review covers applications to plant-derived carbohydrates, N- and O-linked glycans from glycoproteins, glycated proteins, mucins, glycosaminoglycans, bacterial glycolipids, glycosphingolipids, glycoglycerolipids and related compounds, and glycosides. Applications of MALDI mass spectrometry to the study of enzymes acting on carbohydrates (glycosyltransferases and glycosidases) and to the synthesis of carbohydrates, are also covered.

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Untitled

Cited by 14 publications

References 58 publications

Rapid Assembly of Oligosaccharides: A Highly Convergent Strategy for the Assembly of a Glycosylated Amino Acid Derived from PSGL-1

Rapid Assembly of Oligosaccharides: A Highly Convergent Strategy for the Assembly of a Glycosylated Amino Acid Derived from PSGL-1

Enzymatic Biosynthesis of Oligosaccharides and Glycoconjugates

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update covering the period 1999–2000

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