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Synthesis of the saccharide moiety of galactosylgloboside (SSEA-3) and its conjugation to bovine serum albumin and sepharose

Nilsson, Ulf LU and Magnusson, Göran LU (1995) In Carbohydrate Research 272(1). p.9-16
Abstract

The pentasaccharide glycoside corresponding to galactosylgloboside (SSEA-3), β-d-Gal p-(1 → 3)-β-d-Gal pNAc-(1 → 3)-α-d-Gal p-(1 → 4)-β-d-Gal p-(1 → 4)-β-d-Glc p-1-OCH2CH2Si-(CH3)3 (4), was synthesized via glycosylation (87%) of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-[2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-α-d-galactopyranosyl)-β-d- galactopyranosyl]-β-d-glucopyranoside (2) with the glycosyl donor methyl 4,6-di-O-acetyl-2-deoxy-2-phthalimido-3-O-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-1-thio-β-d -galactopyranoside (1), followed by removal of protecting groups. Compound 4 was transformed into the spacer glycoside β-d-Gal p-(1 → 3)-β-d-Gal pNAc-(1 → 3)-α-d-Gal p-(1 → 4)-β-d-Gal... (More)

The pentasaccharide glycoside corresponding to galactosylgloboside (SSEA-3), β-d-Gal p-(1 → 3)-β-d-Gal pNAc-(1 → 3)-α-d-Gal p-(1 → 4)-β-d-Gal p-(1 → 4)-β-d-Glc p-1-OCH2CH2Si-(CH3)3 (4), was synthesized via glycosylation (87%) of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-[2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-α-d-galactopyranosyl)-β-d- galactopyranosyl]-β-d-glucopyranoside (2) with the glycosyl donor methyl 4,6-di-O-acetyl-2-deoxy-2-phthalimido-3-O-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-1-thio-β-d -galactopyranoside (1), followed by removal of protecting groups. Compound 4 was transformed into the spacer glycoside β-d-Gal p-(1 → 3)-β-d-Gal pNAc-(1 → 3)-α-d-Gal p-(1 → 4)-β-d-Gal p-(1 → 4)-β-d-Glcp-1-SCH2CH2COOH (10), which was coupled to bovine serum albumin (BSA), and Sepharose beads, to give the corresponding neoglycoprotein (11, 6 mol of saccharide/mol of BSA) and glycosylated Sepharose (12, 2.7 μmol of saccharide/mL of sedimented beads), respectively. An improved synthesis of a protected globotetraoside β-d-Gal pNAc-(1 → 3)-α-d-Gal p-(1 → 4)-β-d-Gal p-(1 → 4)-β-d-Glc p-1-OCH2CH2SiMe3 is also reported.

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Contribution to journal
publication status
published
subject
keywords
2-(Trimethylsilyl)ethyl glycoside, BSA-conjugate, Galactosylgloboside, Sepharose-conjugate, Thioglycoside donor
in
Carbohydrate Research
volume
272
issue
1
pages
8 pages
publisher
Elsevier
external identifiers
  • scopus:0028991218
  • pmid:7648586
ISSN
0008-6215
DOI
10.1016/0008-6215(95)00044-T
language
English
LU publication?
yes
id
b0923587-06ae-434b-897a-47dbb4104756
date added to LUP
2023-02-07 09:47:58
date last changed
2023-12-20 09:00:48
@article{b0923587-06ae-434b-897a-47dbb4104756,
  abstract     = {{<p>The pentasaccharide glycoside corresponding to galactosylgloboside (SSEA-3), β-d-Gal p-(1 → 3)-β-d-Gal pNAc-(1 → 3)-α-d-Gal p-(1 → 4)-β-d-Gal p-(1 → 4)-β-d-Glc p-1-OCH<sub>2</sub>CH<sub>2</sub>Si-(CH<sub>3</sub>)<sub>3</sub> (4), was synthesized via glycosylation (87%) of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-[2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-α-d-galactopyranosyl)-β-d- galactopyranosyl]-β-d-glucopyranoside (2) with the glycosyl donor methyl 4,6-di-O-acetyl-2-deoxy-2-phthalimido-3-O-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-1-thio-β-d -galactopyranoside (1), followed by removal of protecting groups. Compound 4 was transformed into the spacer glycoside β-d-Gal p-(1 → 3)-β-d-Gal pNAc-(1 → 3)-α-d-Gal p-(1 → 4)-β-d-Gal p-(1 → 4)-β-d-Glcp-1-SCH<sub>2</sub>CH<sub>2</sub>COOH (10), which was coupled to bovine serum albumin (BSA), and Sepharose beads, to give the corresponding neoglycoprotein (11, 6 mol of saccharide/mol of BSA) and glycosylated Sepharose (12, 2.7 μmol of saccharide/mL of sedimented beads), respectively. An improved synthesis of a protected globotetraoside β-d-Gal pNAc-(1 → 3)-α-d-Gal p-(1 → 4)-β-d-Gal p-(1 → 4)-β-d-Glc p-1-OCH<sub>2</sub>CH<sub>2</sub>SiMe<sub>3</sub> is also reported.</p>}},
  author       = {{Nilsson, Ulf and Magnusson, Göran}},
  issn         = {{0008-6215}},
  keywords     = {{2-(Trimethylsilyl)ethyl glycoside; BSA-conjugate; Galactosylgloboside; Sepharose-conjugate; Thioglycoside donor}},
  language     = {{eng}},
  month        = {{07}},
  number       = {{1}},
  pages        = {{9--16}},
  publisher    = {{Elsevier}},
  series       = {{Carbohydrate Research}},
  title        = {{Synthesis of the saccharide moiety of galactosylgloboside (SSEA-3) and its conjugation to bovine serum albumin and sepharose}},
  url          = {{http://dx.doi.org/10.1016/0008-6215(95)00044-T}},
  doi          = {{10.1016/0008-6215(95)00044-T}},
  volume       = {{272}},
  year         = {{1995}},
}